Database of Ru-Catalyzed Ethenolysis of Seed Oils

đź“Š Plot Data
Entry Substrate 1 Substrate 2 Main composition Product 1 Product 2 Homodimer 1 Homodimer 2 Trace products Conv. (%) Sel. (%) Yield (%) TON Class Analytical method Reactor mode Atmosphere T (°C) t (h) Special conditions Solid support Catalyst phase Solvent [Cat.] (ppm) Catalyst PreCat MCB charge mult code_name Label used in reference
1 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 18.9 90.7 17.1 171000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 1c in Gawin2023 (DOI: 10.1021/jacs.3c10635)
2 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 14.5 94.3 13.7 274000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 1c in Gawin2023
3 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 26.2 97.1 25.4 254000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 1d in Gawin2023
4 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 16.4 99.6 16.3 326000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 1d in Gawin2023
5 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 26.2 96.8 25.4 254000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 0 1 CAAC.25 1f in Gawin2023
6 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 17.7 98.3 17.4 348000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 0 1 CAAC.25 1f in Gawin2023
7 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 20.2 71.5 14.5 145000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(CC)cccc3CC)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(CC)cccc3CC)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(CC)cccc3CC)c5ccccc5CC4 0 1 sCAAC.01 5a in Gawin2023
8 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 37.0 86.3 31.9 319000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C)c5ccccc5CC4 0 1 sCAAC.02 5b in Gawin2023
9 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 52.4 95.8 50.2 502000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 5c in Gawin2023
10 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 31.9 96.9 30.9 618000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 5c in Gawin2023
11 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 56.2 95.7 53.8 538000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(OC)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(OC)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(OC)c5CC4 0 1 sCAAC.04 5d in Gawin2023
12 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 49.2 95.7 47.1 471000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccc(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccc(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccc(OC)cc5CC4 0 1 sCAAC.05 5e in Gawin2023
13 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 56.4 94.9 53.5 535000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)ccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)ccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)ccc5CC4 0 1 sCAAC.06 5f in Gawin2023
14 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 66.1 94.2 62.3 623000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 5g in Gawin2023
15 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 50.4 95.6 48.2 964000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 5g in Gawin2023
16 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 53.4 96.0 51.3 513000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(C)ccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(C)ccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(C)ccc5CC4 0 1 sCAAC.08 5h in Gawin2023
17 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 68.2 94.3 64.3 643000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 0 1 sCAAC.09 5i in Gawin2023
18 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 53.2 95.5 50.8 508000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(C)(C)C4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(C)(C)C4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(C)(C)C4 0 1 sCAAC.10 5j in Gawin2023
19 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 55.5 95.1 52.8 528000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(c6ccccc6)C4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(c6ccccc6)C4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(c6ccccc6)C4 0 1 sCAAC.11 5k in Gawin2023
20 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 49.6 96.8 48.0 480000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 5l in Gawin2023
21 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 30.5 97.2 29.6 592000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 5l in Gawin2023
22 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 4.0 96.0 3.8 38000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCC4 0 1 sCAAC.13 1i in Gawin2023
23 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 6.0 98.8 5.9 59000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.18 1j in Gawin2023
24 C=C (10 bar, 99.995%) HOSOME (C16:0, C18:0/1/2/3) C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 22.9 97.4 22.3 223000 O GC, IS: methyl stearate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4c(C)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4c(C)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4c(C)cccc4 0 1 CAAC.54 1k in Gawin2023
25 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 41.0 92.2 37.8 378000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 1c in Gawin2023
26 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 25.2 93.5 23.6 472000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 1c in Gawin2023
27 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 15.6 96.6 15.1 604000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 1c in Gawin2023
28 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 42.7 95.4 40.7 407000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 1d in Gawin2023
29 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 26.3 97.3 25.6 512000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 1d in Gawin2023
30 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 37.0 99.4 36.8 368000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 0 1 CAAC.25 1f in Gawin2023
31 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 26.2 99.6 26.0 520000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 0 1 CAAC.25 1f in Gawin2023
32 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 15.6 99.7 15.6 624000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 0 1 CAAC.25 1f in Gawin2023
33 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 63.9 95.0 60.7 607000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 5c in Gawin2023
34 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 46.1 98.0 45.2 904000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 5c in Gawin2023
35 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 32.2 99.4 32.0 1280000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 5c in Gawin2023
36 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 77.3 91.3 70.6 706000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 5g in Gawin2023
37 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 62.2 95.4 59.3 1190000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 5g in Gawin2023
38 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 45.5 97.2 44.2 1770000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 5g in Gawin2023
39 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 26.4 98.7 26.1 2610000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.1 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 5g in Gawin2023
40 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 76.2 92.7 70.6 706000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 0 1 sCAAC.09 5i in Gawin2023
41 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.3 96.1 57.0 1140000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 0 1 sCAAC.09 5i in Gawin2023
42 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 45.5 97.8 44.5 1780000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 0 1 sCAAC.09 5i in Gawin2023
43 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 26.1 99.3 25.9 2590000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.1 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 0 1 sCAAC.09 5i in Gawin2023
44 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 61.8 96.4 59.6 596000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 5l in Gawin2023
45 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 41.9 98.4 41.2 824000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 5l in Gawin2023
46 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 31.2 99.3 31.0 1240000 P1 GC, IS: methyl stearate semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 5l in Gawin2023
47 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 20.6 71.9 14.8 148000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 1c in Gawin2023
48 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 12.4 68.6 8.5 170000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 1c in Gawin2023
49 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 26.3 77.5 20.4 204000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 1d in Gawin2023
50 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 16.5 74.6 12.3 246000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 1d in Gawin2023
51 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 26.4 75.0 19.8 198000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 0 1 CAAC.25 1f in Gawin2023
52 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 11.9 70.1 8.3 166000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 0 1 CAAC.25 1f in Gawin2023
53 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 36.8 76.0 28.0 280000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C)c5ccccc5CC4 0 1 sCAAC.02 5b in Gawin2023
54 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 54.6 83.9 45.8 458000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 5c in Gawin2023
55 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 32.0 76.3 24.4 488000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 5c in Gawin2023
56 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 53.9 83.3 44.9 449000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(OC)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(OC)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(OC)c5CC4 0 1 sCAAC.04 5d in Gawin2023
57 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 52.8 82.6 43.6 436000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccc(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccc(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccc(OC)cc5CC4 0 1 sCAAC.05 5e in Gawin2023
58 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 60.1 84.8 51.0 510000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)ccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)ccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)ccc5CC4 0 1 sCAAC.06 5f in Gawin2023
59 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 51.3 82.5 42.3 423000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(C)ccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(C)ccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(C)ccc5CC4 0 1 sCAAC.08 5h in Gawin2023
60 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 67.1 85.8 57.6 576000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 5g in Gawin2023
61 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 43.1 78.5 33.8 676000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 5g in Gawin2023
62 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 61.1 85.2 52.1 521000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 0 1 sCAAC.09 5i in Gawin2023
63 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 44.3 81.0 35.9 718000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cccc(Cl)c5CC4 0 1 sCAAC.09 5i in Gawin2023
64 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 57.5 84.4 48.5 485000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(C)(C)C4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(C)(C)C4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(C)(C)C4 0 1 sCAAC.10 5j in Gawin2023
65 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 58.7 84.1 49.4 494000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(c6ccccc6)C4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(c6ccccc6)C4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5C(c6ccccc6)C4 0 1 sCAAC.11 5k in Gawin2023
66 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 47.5 81.7 38.8 388000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 5l in Gawin2023
67 C=C (10 bar, 99.995%) Rapeseed (C16:0, C18:0/1/2/3) C18:1 69%, C18:2 19% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3 oils 35.6 78.1 27.8 556000 O GC, IS: methyl palmitate (residual) semi-batch autoclave None 40 6.0 None None homogeneous neat (catalyst added in 0.2 mL toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 5l in Gawin2023
68 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 35.0 94.0 32.9 329000 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru3 in Afanaseva2025 (DOI: 10.1002/cssc.202402190)
69 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 30.0 96.0 28.8 576000 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru3 in Afanaseva2025
70 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 41.0 98.0 40.2 401800 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 Ru4 in Afanaseva2025
71 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 35.0 98.0 34.3 686000 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 Ru4 in Afanaseva2025
72 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 44.0 89.0 39.2 391600 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 Ru5 in Afanaseva2025
73 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 27.0 99.0 26.7 534600 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 Ru5 in Afanaseva2025
74 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 59.0 93.0 54.9 548700 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 Ru6 in Afanaseva2025
75 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 37.0 98.0 36.3 725200 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 Ru6 in Afanaseva2025
76 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 42.0 97.0 40.7 407400 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 0 1 sCAAC.14 Ru7 in Afanaseva2025
77 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 19.0 99.0 18.8 376200 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 0 1 sCAAC.14 Ru7 in Afanaseva2025
78 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 47.0 97.0 45.6 455900 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 0 1 sCAAC.15 Ru8 in Afanaseva2025
79 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 39.0 98.0 38.2 764400 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 0 1 sCAAC.15 Ru8 in Afanaseva2025
80 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 58.0 97.0 56.3 562600 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 0 1 sCAAC.16 Ru9 in Afanaseva2025
81 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 42.0 98.0 41.2 823200 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 0 1 sCAAC.16 Ru9 in Afanaseva2025
82 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 40.0 98.0 39.2 392000 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 0 1 sCAAC.17 Ru10 in Afanaseva2025
83 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 35.0 98.0 34.3 686000 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 0 1 sCAAC.17 Ru10 in Afanaseva2025
84 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 31.0 95.0 29.5 294500 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 0 1 sCAAC.18 Ru11 in Afanaseva2025
85 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 16.0 99.0 15.8 316800 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 0 1 sCAAC.18 Ru11 in Afanaseva2025
86 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 44.0 99.0 43.6 435600 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
87 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 29.0 99.0 28.7 574200 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
88 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 42.0 97.0 40.7 814800 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 Ru4 in Afanaseva2025
89 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 39.0 98.0 38.2 764400 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 Ru4 in Afanaseva2025
90 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 49.0 97.0 47.5 950600 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 Ru5 in Afanaseva2025
91 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 46.0 97.0 44.6 892400 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 Ru5 in Afanaseva2025
92 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 41.0 97.0 39.8 795400 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 Ru6 in Afanaseva2025
93 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 37.0 98.0 36.3 725200 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 Ru6 in Afanaseva2025
94 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 40.0 97.0 38.8 776000 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 0 1 sCAAC.14 Ru7 in Afanaseva2025
95 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 44.0 97.0 42.7 853600 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 0 1 sCAAC.14 Ru7 in Afanaseva2025
96 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 28.0 97.0 27.2 543200 S1 GC, IS: methyl palmitate (residual) batch reactor None 70 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 0 1 sCAAC.14 Ru7 in Afanaseva2025
97 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 48.0 98.0 47.0 940800 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 0 1 sCAAC.15 Ru8 in Afanaseva2025
98 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 29.0 99.0 28.7 574200 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 0 1 sCAAC.15 Ru8 in Afanaseva2025
99 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 17.0 99.0 16.8 336600 S1 GC, IS: methyl palmitate (residual) batch reactor None 30 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 0 1 sCAAC.16 Ru9 in Afanaseva2025
100 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 40.0 98.0 39.2 784000 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 0 1 sCAAC.16 Ru9 in Afanaseva2025
101 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 30.0 99.0 29.7 594000 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 0 1 sCAAC.16 Ru9 in Afanaseva2025
102 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 38.0 97.0 36.9 737200 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 0 1 sCAAC.17 Ru10 in Afanaseva2025
103 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 36.0 98.0 35.3 705600 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 0 1 sCAAC.17 Ru10 in Afanaseva2025
104 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 50.0 97.0 48.5 970000 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 0 1 sCAAC.18 Ru11 in Afanaseva2025
105 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 56.0 98.0 54.9 1097600 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 0 1 sCAAC.18 Ru11 in Afanaseva2025
106 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 40.0 97.0 38.8 776000 S1 GC, IS: methyl palmitate (residual) batch reactor None 70 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 0 1 sCAAC.18 Ru11 in Afanaseva2025
107 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 30.0 99.0 29.7 594000 S1 GC, IS: methyl palmitate (residual) batch reactor None 15 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
108 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 31.0 99.0 30.7 613800 S1 GC, IS: methyl palmitate (residual) batch reactor None 30 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
109 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 28.0 99.0 27.7 554400 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
110 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 19.0 99.0 18.8 376200 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
111 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 51.0 99.0 50.5 504900 S1 GC, IS: methyl palmitate (residual) batch reactor None 15 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
112 C=C (10 bar, 99.95%) FAMEs (C16:0, C18:0/1/2/3, C20:1) C18:1 84% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2/3, C20:1 oils 55.0 99.0 54.5 363000 S1 GC, IS: methyl palmitate (residual) batch reactor None 15 5.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 1.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
113 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 45.0 96.0 43.2 864000 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CC4 0 1 sCAAC.03 Ru4 in Afanaseva2025
114 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 73.0 95.0 69.4 1387000 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 Ru5 in Afanaseva2025
115 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 42.0 98.0 41.2 1646400 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5CCC4 0 1 sCAAC.12 Ru5 in Afanaseva2025
116 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 72.0 94.0 67.7 1353600 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 Ru6 in Afanaseva2025
117 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 40.0 97.0 38.8 1552000 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc(OC)c(OC)cc5CC4 0 1 sCAAC.07 Ru6 in Afanaseva2025
118 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 56.0 97.0 54.3 1086400 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5c(C)ccc(C)c5CC4 0 1 sCAAC.14 Ru7 in Afanaseva2025
119 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.0 96.0 56.6 1132800 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCc6cc5CC4 0 1 sCAAC.15 Ru8 in Afanaseva2025
120 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 66.0 96.0 63.4 1267200 S1 GC, IS: methyl palmitate (residual) batch reactor None 40 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCOc6cc5CC4 0 1 sCAAC.16 Ru9 in Afanaseva2025
121 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 69.0 95.0 65.6 1311000 S1 GC, IS: methyl palmitate (residual) batch reactor None 50 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6OCCOc6cc5CC4 0 1 sCAAC.17 Ru10 in Afanaseva2025
122 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 84.0 94.0 79.0 1579200 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 0 1 sCAAC.18 Ru11 in Afanaseva2025
123 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 97.0 49.5 1978800 S1 GC, IS: methyl palmitate (residual) batch reactor None 60 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.25 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5cc6CCCCc6cc5CC4 0 1 sCAAC.18 Ru11 in Afanaseva2025
124 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 65.0 98.0 63.7 1274000 S1 GC, IS: methyl palmitate (residual) batch reactor None 15 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
125 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 63.0 98.0 61.7 1234800 S1 GC, IS: methyl palmitate (residual) batch reactor None 25 6.0 None None homogeneous neat (catalyst added in 0.001 M toluene solution) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)c5ccccc5OCC4 0 1 sCAAC.19 Ru12 in Afanaseva2025
126 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 97.0 19.0 360000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 Ru5 in Sytniczuk2023a (DOI: 10.1016/j.checat.2023.100713)
127 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 11.0 97.0 11.0 219000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 Ru5 in Sytniczuk2023a
128 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 49.0 96.0 48.0 158000 S1 GC, IS: methyl stearate batch autoclave air 40 6.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 Ru5 in Sytniczuk2023a
129 C=C (10 bar, 99.95%) FAME (C18:0/1/2) C18:1 73%, C18:2 20% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 17.0 99.0 17.0 57000 O GC, IS: methyl stearate batch autoclave argon 40 6.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 Ru5 in Sytniczuk2023a
130 C=C (10 bar, 99.95%) FAME (C18:0/1/2) C18:1 73%, C18:2 20% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 65.0 96.0 63.0 42000 O GC, IS: methyl stearate batch autoclave air 40 6.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 15.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 Ru5 in Sytniczuk2023a
131 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 83.0 88.0 73.0 244000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru6 in Sytniczuk2023a
132 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 40.0 93.0 37.0 744000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru6 in Sytniczuk2023a
133 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 40.0 94.0 37.0 743000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru6 in Sytniczuk2023a
134 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 70.0 90.0 63.0 211000 S1 GC, IS: methyl stearate batch autoclave air 40 6.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru6 in Sytniczuk2023a
135 C=C (10 bar, 99.95%) FAME (C18:0/1/2) C18:1 73%, C18:2 20% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 27.0 99.0 27.0 89000 O GC, IS: methyl stearate batch autoclave argon 40 6.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru6 in Sytniczuk2023a
136 C=C (10 bar, 99.95%) FAME (C18:0/1/2) C18:1 73%, C18:2 20% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 86.0 91.0 78.0 52000 O GC, IS: methyl stearate batch autoclave air 40 6.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 15.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru6 in Sytniczuk2023a
137 C=C (10 bar, 99.95%) FAME (C18:0/1/2) C18:1 73%, C18:2 20% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 89.0 90.0 80.0 54000 O GC, IS: methyl stearate batch autoclave argon 40 6.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 15.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3)(C)c4ccccc4 0 1 CAAC.35 Ru6 in Sytniczuk2023a
138 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 81.0 89.0 72.0 242000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)CC)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)CC)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)CC)cccc3)(C)c4ccccc4 0 1 CAAC.36 Ru7 in Sytniczuk2023a
139 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 29.0 93.0 27.0 536000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)CC)cccc3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)CC)cccc3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)CC)cccc3)(C)c4ccccc4 0 1 CAAC.36 Ru7 in Sytniczuk2023a
140 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 80.0 90.0 72.0 240000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccccc4 0 1 CAAC.37 Ru8 in Sytniczuk2023a
141 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 23.0 90.0 20.0 409000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccccc4 0 1 CAAC.37 Ru8 in Sytniczuk2023a
142 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 80.0 89.0 71.0 237000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4c5ccccc5ccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4c5ccccc5ccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4c5ccccc5ccc4 0 1 CAAC.38 Ru9 in Sytniczuk2023a
143 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 38.0 95.0 36.0 723000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4c5ccccc5ccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4c5ccccc5ccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4c5ccccc5ccc4 0 1 CAAC.38 Ru9 in Sytniczuk2023a
144 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 56.0 35.0 20.0 65000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)(C) 0 1 CAAC.39 Ru10 in Sytniczuk2023a
145 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 13.0 8.0 1.0 20000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst solution, 1 mg/mL) 0.5 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)(C) 0 1 CAAC.39 Ru10 in Sytniczuk2023a
146 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 42.0 96.0 43.0 144000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 Ru1 in Sytniczuk2023b (DOI: 10.1039/d3sc03849a)
147 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 28.0 97.0 27.0 274000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 Ru1 in Sytniczuk2023b
148 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 36.0 90.0 32.0 107000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.30 Ru11 in Sytniczuk2023b
149 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 18.0 89.0 16.0 160000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.30 Ru11 in Sytniczuk2023b
150 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 54.0 91.0 49.0 164000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.31 Ru12 in Sytniczuk2023b
151 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 24.0 92.0 22.0 221000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.31 Ru12 in Sytniczuk2023b
152 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 87.0 87.0 76.0 25000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 30.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.32 Ru13 in Sytniczuk2023b
153 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 79.0 90.0 71.0 35000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.32 Ru13 in Sytniczuk2023b
154 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 57.0 95.0 54.0 181000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.32 Ru13 in Sytniczuk2023b
155 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 38.0 96.0 36.0 362000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.32 Ru13 in Sytniczuk2023b
156 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 68.0 87.0 59.0 197000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.33 Ru14 in Sytniczuk2023b
157 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 30.0 90.0 27.0 274000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)ccc(C(C)(C)C)c3)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.33 Ru14 in Sytniczuk2023b
158 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 55.0 97.0 54.0 179000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.34 Ru15 in Sytniczuk2023b
159 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 27.0 99.0 27.0 270000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccc(CC(C)C)cc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccc(CC(C)C)cc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccc(CC(C)C)cc4 0 1 CAAC.34 Ru15 in Sytniczuk2023b
160 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 53.0 96.0 51.0 170000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 Ru8 in Sytniczuk2023c (DOI: 10.1039/d3cy00395g)
161 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 61.0 95.0 58.0 192000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)CC)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)CC)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)CC)cccc3C)(C)c4ccccc4 0 1 CAAC.26 Ru10 in Sytniczuk2023c
162 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.0 93.0 55.0 55000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)CC)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)CC)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)CC)cccc3C)(C)c4ccccc4 0 1 CAAC.26 Ru10 in Sytniczuk2023c
163 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 60.0 93.0 56.0 186000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)CC)cc(C)cc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)CC)cc(C)cc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)CC)cc(C)cc3C)(C)c4ccccc4 0 1 CAAC.27 Ru11 in Sytniczuk2023c
164 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.0 92.0 54.0 54000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)CC)cc(C)cc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)CC)cc(C)cc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)CC)cc(C)cc3C)(C)c4ccccc4 0 1 CAAC.27 Ru11 in Sytniczuk2023c
165 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 44.0 89.0 39.0 132000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CCC)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CCC)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CCC)cccc3C)(C)c4ccccc4 0 1 CAAC.28 Ru12 in Sytniczuk2023c
166 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 69.0 84.0 58.0 58000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CCC)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CCC)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CCC)cccc3C)(C)c4ccccc4 0 1 CAAC.28 Ru12 in Sytniczuk2023c
167 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 35.0 92.0 33.0 108000 S1 GC, IS: methyl stearate batch autoclave None 40 6.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CCC)cccc3CCC)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CCC)cccc3CCC)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CCC)cccc3CCC)(C)c4ccccc4 0 1 CAAC.29 Ru13 in Sytniczuk2023c
168 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 71.0 88.0 63.0 63000 S1 GC, IS: methyl stearate batch autoclave None 40 3.0 None None homogeneous toluene (anhydrous; catalyst stock solution, 5 mL) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CCC)cccc3CCC)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CCC)cccc3CCC)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CCC)cccc3CCC)(C)c4ccccc4 0 1 CAAC.29 Ru13 in Sytniczuk2023c
169 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 89.0 88.0 79.0 15700 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) 0 1 CAAC.40 2a in Kim2022 (DOI: 10.1021/acs.organomet.2c00153)
170 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 46.0 94.0 44.0 44800 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) 0 1 CAAC.40 2a in Kim2022
171 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 21.0 96.0 20.0 40900 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(c5ccccc5N2C(c3ccccc3)c4ccccc4)(CC)(CC) 0 1 CAAC.40 2a in Kim2022
172 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 91.0 91.0 84.0 16800 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) 0 1 CAAC.41 2e in Kim2022
173 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 46.0 91.0 42.0 42600 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) 0 1 CAAC.41 2e in Kim2022
174 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 32.0 92.0 30.0 59633 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) 0 1 CAAC.41 2e in Kim2022
175 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 23.0 94.0 22.0 56400 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 4.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) 0 1 CAAC.41 2e in Kim2022
176 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 95.0 18.0 61200 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(c4ccccc4N2Cc3ccccc3)(CC)(CC) 0 1 CAAC.41 2e in Kim2022
177 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 63.0 30.0 19.0 1900 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 0 1 CAAC.42 2f in Kim2022
178 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 25.0 13.0 2600 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 0 1 CAAC.42 2f in Kim2022
179 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 14.0 27.0 4.0 4100 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C6(c5ccccc5N2C(c3ccccc3)c4ccccc4)CCCCC6 0 1 CAAC.42 2f in Kim2022
180 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 95.0 94.7 90.0 90 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.0 None en-HG2@capsule-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022 (DOI: 10.1039/d2cy01291j)
181 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 72.0 98.6 71.0 142 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.5 None en-HG2@capsule-SiO2 heterogeneous toluene 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
182 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 89.0 98.9 88.0 88 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 0.5 None HG2@capsule-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
183 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 93.0 97.8 91.0 91 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.0 None en-HG2@peanut-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
184 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 70.0 100.0 70.0 140 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.5 None en-HG2@peanut-SiO2 heterogeneous toluene 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
185 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 90.0 100.0 90.0 90 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.0 None HG2@peanut-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
186 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 98.0 95.9 94.0 94 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.0 None en-HG2@square-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
187 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 76.0 97.4 74.0 148 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.5 None en-HG2@square-SiO2 heterogeneous toluene 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
188 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 91.0 100.0 91.0 91 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.0 None HG2@square-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
189 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 89.0 93.3 83.0 83 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 4.0 None en-HG2@commercial-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
190 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 98.0 93.9 92.0 92 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 1.5 None None homogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
191 C=C (1 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 70% (technical) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 45.0 100.0 45.0 45 P1 GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None None homogeneous toluene 10000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 G1 in Askun2022
192 C=C (1 bar) FAME from Corn (C16:0, C18:0/1/2) C18:1 30%, C18:2 51% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 99.0 99.0 98.0 98 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@capsule-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
193 C=C (1 bar) FAME from Rapeseed (C16:0, C18:0/1/2) C18:1 62%, C18:2 25% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 99.0 100.0 99.0 99 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@capsule-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
194 C=C (1 bar) FAME from Coffee (C16:0, C18:0/1/2) C18:1 11%, C18:2 34% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 94.0 100.0 94.0 94 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@capsule-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
195 C=C (1 bar) FAME from Corn (C16:0, C18:0/1/2) C18:1 30%, C18:2 51% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 99.0 98.0 97.0 97 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@peanut-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
196 C=C (1 bar) FAME from Rapeseed (C16:0, C18:0/1/2) C18:1 62%, C18:2 25% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 99.0 99.0 98.0 98 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@peanut-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
197 C=C (1 bar) FAME from Coffee (C16:0, C18:0/1/2) C18:1 11%, C18:2 34% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 96.0 100.0 96.0 96 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@peanut-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
198 C=C (1 bar) FAME from Corn (C16:0, C18:0/1/2) C18:1 30%, C18:2 51% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 99.0 99.0 98.0 98 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@square-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
199 C=C (1 bar) FAME from Rapeseed (C16:0, C18:0/1/2) C18:1 62%, C18:2 25% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 99.0 97.0 96.0 96 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@square-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
200 C=C (1 bar) FAME from Coffee (C16:0, C18:0/1/2) C18:1 11%, C18:2 34% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 95.0 98.9 94.0 94 O GC, IS: n-tetradecane batch Schlenk tube None 80 3.0 None en-HG2@square-SiO2 heterogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
201 C=C (1 bar) FAME from Corn (C16:0, C18:0/1/2) C18:1 30%, C18:2 51% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 99.0 91.9 91.0 91 O GC, IS: n-tetradecane batch Schlenk tube None 80 1.0 None None homogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
202 C=C (1 bar) FAME from Rapeseed (C16:0, C18:0/1/2) C18:1 62%, C18:2 25% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 99.0 90.9 90.0 90 O GC, IS: n-tetradecane batch Schlenk tube None 80 1.0 None None homogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
203 C=C (1 bar) FAME from Coffee (C16:0, C18:0/1/2) C18:1 11%, C18:2 34% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 98.0 91.8 90.0 90 O GC, IS: n-tetradecane batch Schlenk tube None 80 1.0 None None homogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Askun2022
204 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 1.0 92.0 1.0 230 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)C)cccc2C(C)C)N(C(C)C)C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)C)cccc2C(C)C)N(C(C)C)C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)C)cccc2C(C)C)N(C(C)C)C(C)C 0 1 AAOC.1 4a in Byun2022 (DOI: 10.1039/d1qi01132d)
205 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 82.0 89.0 73.0 14500 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)C)cccc2C(C)C)N3CCCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)C)cccc2C(C)C)N3CCCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)C)cccc2C(C)C)N3CCCCC3 0 1 AAOC.2 4b in Byun2022
206 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 80.0 90.0 72.0 14000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)C)cccc2C(C)C)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)C)cccc2C(C)C)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)C)cccc2C(C)C)N3CCCC3 0 1 AAOC.3 4c in Byun2022
207 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 86.0 91.0 78.0 16000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
208 C=C (14 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 88.0 95.0 84.0 17000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
209 C=C (14 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 86.0 96.0 82.0 41000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
210 C=C (21 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 78.0 98.0 77.0 38000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
211 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 82.0 95.0 78.0 39000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
212 C=C (21 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 66.0 98.0 65.0 65000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
213 C=C (14 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 72.0 97.0 70.0 70000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
214 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 70.0 95.0 67.0 67000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
215 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 52.0 97.0 50.0 100000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](Oc2c(C(C)(C)C)cccc2CCC)N3CCCC3 0 1 AAOC.4 4d in Byun2022
216 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 1.0 62.0 1.0 100 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C(N(C)c2c(C(C)C)cccc2C(C)C)N(C)c3c(C(C)C)cccc3C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C](N(C)c2c(C(C)C)cccc2C(C)C)N(C)c3c(C(C)C)cccc3C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C](N(C)c2c(C(C)C)cccc2C(C)C)N(C)c3c(C(C)C)cccc3C(C)C 0 1 dAC 15 in Byun2022
217 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 63.0 95.0 60.0 20000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 30.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.117 10a in Byun2020 (DOI: 10.1021/acscatal.0c02018)
218 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 4.0 98.0 4.0 4000 S1 GC, IS: tridecane batch reactor None 40 3.0 None None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.117 10a in Byun2020
219 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 33.0 98.0 32.0 32000 S1 GC, IS: tridecane batch reactor None 40 3.0 An impurity was present None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.117 10a in Byun2020
220 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 46.0 98.0 45.0 45000 S1 GC, IS: tridecane batch reactor None 40 3.0 10 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.117 10a in Byun2020
221 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 30.0 97.0 29.0 58000 S1 GC, IS: tridecane batch reactor None 40 3.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.117 10a in Byun2020
222 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 97.0 19.0 63000 S1 GC, IS: tridecane batch reactor None 40 6.0 3 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.117 10a in Byun2020
223 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 14.0 98.0 14.0 28000 S1 GC, IS: tridecane batch reactor None 40 3.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccc(C(C)(C)C)cc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(C(C)(C)C)cc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(C(C)(C)C)cc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.118 10b in Byun2020
224 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 21.0 96.0 20.0 40000 S1 GC, IS: tridecane batch reactor None 40 6.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccc(OC)cc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(OC)cc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(OC)cc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.119 10c in Byun2020
225 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 32.0 97.0 31.0 62000 S1 GC, IS: tridecane batch reactor None 40 3.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccc(F)cc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(F)cc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(F)cc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.120 10d in Byun2020
226 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 21.0 98.0 21.0 42000 S1 GC, IS: tridecane batch reactor None 40 3.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccc(C(F)(F)F)cc5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(C(F)(F)F)cc5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(C(F)(F)F)cc5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.121 10e in Byun2020
227 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 18.0 97.0 17.0 35000 S1 GC, IS: tridecane batch reactor None 40 3.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5cc(C(C)(C)C)cc(C(C)(C)C)c5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5cc(C(C)(C)C)cc(C(C)(C)C)c5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5cc(C(C)(C)C)cc(C(C)(C)C)c5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.122 10f in Byun2020
228 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 20.0 98.0 20.0 40000 S1 GC, IS: tridecane batch reactor None 40 3.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5cc(C(F)(F)F)cc(C(F)(F)F)c5)[n+]2(c3c(C(C)C)cccc3(C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5cc(C(F)(F)F)cc(C(F)(F)F)c5)N2(c3c(C(C)C)cccc3(C(C)C)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5cc(C(F)(F)F)cc(C(F)(F)F)c5)N2(c3c(C(C)C)cccc3(C(C)C)) 0 1 NHC.123 10g in Byun2020
229 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 99.0 19.0 38000 S1 GC, IS: tridecane batch reactor None 40 6.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(CC)CC)cccc3(C(CC)CC)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(CC)CC)cccc3(C(CC)CC)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(CC)CC)cccc3(C(CC)CC)) 0 1 NHC.124 10h in Byun2020
230 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 26.0 95.0 24.0 48000 S1 GC, IS: tridecane batch reactor None 40 6.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccc(F)cc5)[n+]2(c3c(C(CC)CC)cccc3(C(CC)CC)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(F)cc5)N2(c3c(C(CC)CC)cccc3(C(CC)CC)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(F)cc5)N2(c3c(C(CC)CC)cccc3(C(CC)CC)) 0 1 NHC.125 10i in Byun2020
231 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 17.0 93.0 15.0 30000 S1 GC, IS: tridecane batch reactor None 40 3.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)C)cccc3(CCC)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(CCC)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)C)cccc3(CCC)) 0 1 NHC.126 10j in Byun2020
232 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 37.0 95.0 35.0 70000 S1 GC, IS: tridecane batch reactor None 40 6.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)(C)C)cccc3(CCC)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)(C)C)cccc3(CCC)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)(C)C)cccc3(CCC)) 0 1 NHC.127 10k in Byun2020
233 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 97.0 19.0 63000 S1 GC, IS: tridecane batch reactor None 40 6.0 3 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccccc5)[n+]2(c3c(C(C)(C)C)cccc3(CCC)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)(C)C)cccc3(CCC)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccccc5)N2(c3c(C(C)(C)C)cccc3(CCC)) 0 1 NHC.127 10k in Byun2020
234 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 45.0 95.0 43.0 86000 S1 GC, IS: tridecane batch reactor None 40 6.0 5 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccc(F)cc5)[n+]2(c3c(C(C)(C)C)cccc3(CCC)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(F)cc5)N2(c3c(C(C)(C)C)cccc3(CCC)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(F)cc5)N2(c3c(C(C)(C)C)cccc3(CCC)) 0 1 NHC.128 10l in Byun2020
235 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 33.0 95.0 32.0 110000 S1 GC, IS: tridecane batch reactor None 40 6.0 3 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2c4c(F)ccc[n-]4c(c5ccc(F)cc5)[n+]2(c3c(C(C)(C)C)cccc3(CCC)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(F)cc5)N2(c3c(C(C)(C)C)cccc3(CCC)) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2[C]4C(F)=CC=CN4[C](c5ccc(F)cc5)N2(c3c(C(C)(C)C)cccc3(CCC)) 0 1 NHC.128 10l in Byun2020
236 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 50.0 90.0 45.0 150000 S1 GC, IS: tridecane batch reactor None 40 3.0 3 ppm of Cy3P-CuCl (stock in CH2Cl2) None homogeneous toluene (catalyst stock solution, 0.0005 M) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 4a in Byun2020
237 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 6.0 86.0 5.0 550 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cccc4c[n+]2(c3c(C(C)C)cccc3C(C)C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)C)cccc3C(C)C)C=C4C=CC=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)C)cccc3C(C)C)C=C4C=CC=C(F)N24 0 1 NHC.107 Ru5a in Byun2019 (DOI: 10.1021/acs.organomet.9b00469)
238 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 20.0 78.0 15.0 1500 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cccc4c[n+]2(c3c(CC)cccc3CC)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(CC)cccc3CC)C=C4C=CC=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(CC)cccc3CC)C=C4C=CC=C(F)N24 0 1 NHC.108 Ru5b in Byun2019
239 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 14.0 74.0 10.0 1000 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cccc4c[n+]2(c3c(CC)cccc3C)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(CC)cccc3C)C=C4C=CC=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(CC)cccc3C)C=C4C=CC=C(F)N24 0 1 NHC.109 Ru5c in Byun2019
240 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 26.0 82.0 22.0 2200 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cccc4c[n+]2(c3c(C(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)C)cccc3)C=C4C=CC=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)C)cccc3)C=C4C=CC=C(F)N24 0 1 NHC.110 Ru5d in Byun2019
241 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 44.0 79.0 34.0 3400 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cccc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=CC=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=CC=C(F)N24 0 1 NHC.111 Ru5e in Byun2019
242 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 77.0 39.0 3900 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
243 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 32.0 77.0 25.0 5100 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
244 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 71.0 13.0 6700 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
245 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 68.0 79.0 54.0 2700 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
246 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 69.0 84.0 58.0 1200 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
247 C=C (21 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 62.0 83.0 52.0 2600 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
248 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 25.0 77.0 19.0 1900 S1 GC, IS: tridecane batch reactor None 40 12.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
249 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 55.0 76.0 42.0 4200 S1 GC, IS: tridecane batch reactor None 80 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
250 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 57.0 72.0 40.0 4000 S1 GC, IS: tridecane batch reactor None 100 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
251 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 74.0 82.0 60.0 1200 S1 GC, IS: tridecane batch reactor None 80 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
252 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 55.0 82.0 45.0 900 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
253 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 14.0 84.0 12.0 1200 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(C(C)(C)C)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(C(C)(C)C)C=C(F)N24 0 1 NHC.112 Ru5f in Byun2019
254 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 34.0 81.0 27.0 2700 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(OC)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(OC)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(OC)C=C(F)N24 0 1 NHC.113 Ru5g in Byun2019
255 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 27.0 83.0 23.0 2300 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(F)cc(Cl)cc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(Cl)C=C(F)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=C(Cl)C=C(F)N24 0 1 NHC.114 Ru5h in Byun2019
256 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 0.0 0.0 0.0 0 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(Cl)cccc4c[n+]2(c3c(C(C)(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=CC=C(Cl)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)(C)C)cccc3)C=C4C=CC=C(Cl)N24 0 1 NHC.115 Ru6 in Byun2019
257 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 7.0 91.0 6.0 600 S1 GC, IS: tridecane batch reactor None 60 3.0 None None homogeneous toluene (catalyst stock solution, 0.002 M) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)c2[n-]4c(C)cccc4c[n+]2(c3c(C(C)C)cccc3)) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(c3c(C(C)C)cccc3)C=C4C=CC=C(C)N24 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3c(C(C)C)cccc3)C=C4C=CC=C(C)N24 0 1 NHC.116 Ru7a in Byun2019
258 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 5.0 60.0 3.0 3 O GC, IS: undecane batch reactor None 60 16.0 a propenylbenzene as substrate None homogeneous THF 10000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 GI in Avendano2021 (DOI: 10.1016/j.mcat.2021.111631)
259 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 30.0 86.7 26.0 26 O GC, IS: undecane batch reactor None 60 16.0 a propenylbenzene as substrate None homogeneous THF 10000.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 GII in Avendano2021
260 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 99.0 94.9 94.0 94 O GC, IS: undecane batch reactor None 60 16.0 a propenylbenzene as substrate None homogeneous THF 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HII in Avendano2021
261 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 89.0 98.9 88.0 88 O GC, IS: undecane batch reactor None 60 16.0 a propenylbenzene as substrate None homogeneous THF 10000.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.011 M73 in Avendano2021
262 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 99.0 98.0 97.0 97 O GC, IS: undecane batch reactor None 60 16.0 a propenylbenzene as substrate None homogeneous THF 10000.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
263 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 99.0 100.0 99.0 99 O GC, IS: undecane batch reactor None 60 16.0 a propenylbenzene as substrate None homogeneous toluene 10000.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
264 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 99.0 100.0 99.0 99 O GC, IS: undecane batch reactor None 60 2.0 a propenylbenzene as substrate None homogeneous toluene 10000.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
265 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 97.0 99.0 96.0 1920 O GC, IS: undecane batch reactor None 60 2.0 a propenylbenzene as substrate None homogeneous toluene 500.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
266 C=C (10 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 88.0 98.9 87.0 8700 O GC, IS: undecane batch reactor None 60 2.0 a propenylbenzene as substrate None homogeneous toluene 100.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
267 C=C (5 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 97.0 99.0 96.0 1920 O GC, IS: undecane batch reactor None 60 2.0 a propenylbenzene as substrate None homogeneous toluene 500.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
268 C=C (5 bar, 99.9%) c1cc(OC)ccc1C=CC 99% c1cc(OC)ccc1C=C CC=C c1cc(OC)ccc1C=Cc1ccc(OC)cc1 CC=CC c1cc(OC)ccc1CC=C 81.0 98.8 80.0 1600 O GC, IS: undecane batch reactor None 60 2.0 a propenylbenzene as substrate None homogeneous toluene, untreated anethole 500.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
269 C=C (5 bar, 99.9%) c1cc(O)c(OC)cc1C=CC 99% c1cc(O)c(OC)cc1C=C CC=C c1cc(O)c(OC)cc1C=Cc1cc(OC)c(O)cc1 CC=CC None 98.0 99.0 97.0 1940 O GC, IS: undecane batch reactor None 60 2.0 a propenylbenzene as substrate None homogeneous toluene 500.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
270 C=C (5 bar, 99.9%) c1cc(OC)c(OC)cc1C=CC 99% c1cc(OC)c(OC)cc1C=C CC=C c1cc(OC)c(OC)cc1C=Cc1cc(OC)c(OC)cc1 CC=CC None 97.0 99.0 96.0 1920 O GC, IS: undecane batch reactor None 60 2.0 a propenylbenzene as substrate None homogeneous toluene 500.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.005 M73Pr in Avendano2021
271 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 90% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 89.0 49.8 44.3 4427 P1 GC batch autoclave None 40 4.0 TON from distillation None homogeneous toluene 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 Ru1 in Kajetanowicz2020 (DOI: 10.1002/ejlt.201900263)
272 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 90% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 75.0 50.8 38.1 7624 P1 GC batch autoclave None 40 4.0 TON from distillation None homogeneous toluene 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 Ru1 in Kajetanowicz2020
273 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 90% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 54.0 0.0 0.0 0 P1 GC batch autoclave None 40 4.0 TON from distillation None homogeneous toluene 25.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 Ru1 in Kajetanowicz2020
274 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 90% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 53.0 50.9 27.0 10809 P1 GC batch autoclave None 50 4.0 TON from distillation None homogeneous toluene 25.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 Ru1 in Kajetanowicz2020
275 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 90% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 50.0 0.0 0.0 0 P1 GC batch autoclave None 60 4.0 TON from distillation None homogeneous toluene 25.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 Ru1 in Kajetanowicz2020
276 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 90% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 51.0 0.0 0.0 0 P1 GC batch autoclave None 50 2.0 TON from distillation None homogeneous toluene 25.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 Ru1 in Kajetanowicz2020
277 C=C (4 bar, 99.9%) used-cooking-oil FAME (C16:0/1, C18:0/1/2/3) C16:0 11%, C18:1 48%, C18:2 33% (oil 97%) mixture esters/olefins None None None None 96.0 67.1 64.4 14140 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 50.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020 (DOI: 10.1016/j.jiec.2020.01.002)
278 C=C (4 bar, 99.9%) used-cooking-oil FAME (C16:0/1, C18:0/1/2/3) C16:0 11%, C18:1 48%, C18:2 33% (oil 97%) mixture esters/olefins None None None None 68.3 89.6 61.2 37930 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 20.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
279 C=C (4 bar, 99.9%) used-cooking-oil FAME (C16:0/1, C18:0/1/2/3) C16:0 11%, C18:1 48%, C18:2 33% (oil 97%) mixture esters/olefins None None None None 52.7 96.0 50.6 62740 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 10.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
280 C=C (4 bar, 99.9%) used-cooking-oil FAME (C16:0/1, C18:0/1/2/3) C16:0 11%, C18:1 48%, C18:2 33% (oil 97%) mixture esters/olefins None None None None 59.4 76.9 45.7 78080 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 7.5 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
281 C=C (4 bar, 99.9%) used-cooking-oil FAME (C16:0/1, C18:0/1/2/3) C16:0 11%, C18:1 48%, C18:2 33% (oil 97%) mixture esters/olefins None None None None 35.4 87.6 31.0 76880 O GC batch reactor nitrogen 50 0.3 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 5.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
282 C=C (4 bar, 99.9%) chicken-fats FAME (C16:0/1, C18:0/1/2/3) C16:0 23%, C16:1 8%, C18:1 40%, C18:2 21% (oil 98%) mixture esters/olefins None None None None 82.0 89.1 73.1 14630 O GC batch reactor nitrogen 50 0.02 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Pradhan2020
283 C=C (4 bar, 99.9%) chicken-fats FAME (C16:0/1, C18:0/1/2/3) C16:0 23%, C16:1 8%, C18:1 40%, C18:2 21% (oil 98%) mixture esters/olefins None None None None 53.0 85.5 45.3 21820 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Pradhan2020
284 C=C (4 bar, 99.9%) chicken-fats FAME (C16:0/1, C18:0/1/2/3) C16:0 23%, C16:1 8%, C18:1 40%, C18:2 21% (oil 98%) mixture esters/olefins None None None None 41.0 77.8 31.9 16730 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 20.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
285 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 96.0 87.0 83.5 21710 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Pradhan2020
286 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 94.0 66.6 62.6 40710 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Pradhan2020
287 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 95.0 88.2 83.8 72630 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 15.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Pradhan2020
288 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 93.0 76.3 71.0 92000 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Pradhan2020
289 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 67.6 99.7 67.4 44170 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 20.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
290 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 62.5 82.9 51.8 45270 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 15.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
291 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 68.8 86.3 59.4 77800 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 10.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
292 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 68.3 70.6 48.2 84190 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 7.5 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
293 C=C (4 bar, 99.9%) canola-oil FAME (C16:0/1, C18:0/1/2/3) C18:1 64%, C18:2 20%, C18:3 10% (oil 99%) mixture esters/olefins None None None None 18.7 69.0 12.9 35290 O GC batch reactor nitrogen 50 0.5 microwave heating, large-scale (100�150 g substrate) None homogeneous neat (no solvent specified) 5.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Pradhan2020
294 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 0.3 81.0 0.2 116 S1 GC, IS: dodecane batch reactor None 40 4.3 None None homogeneous toluene 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.43 3a in Samkian2020 (DOI: 10.1021/acs.organomet.9b00862)
295 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 0.7 80.0 0.5 257 S1 GC, IS: dodecane batch reactor None 40 4.6 None None homogeneous toluene 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CCC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CCC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CCC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(CC)(CC) 0 1 CAAC.44 3b in Samkian2020
296 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 3.7 93.0 3.4 1720 S1 GC, IS: dodecane batch reactor None 40 4.6 None None homogeneous toluene 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C)CCCCC4 0 1 CAAC.45 3c in Samkian2020
297 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 1.0 80.0 0.8 407 S1 GC, IS: dodecane batch reactor None 60 5.4 None None homogeneous toluene 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CCC(C)(C)N2c3c(C(C)C)cccc3C)CCCCC4 0 1 CAAC.45 3c in Samkian2020
298 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 4.4 77.0 3.4 1705 S1 GC, IS: dodecane batch reactor None 40 4.6 None None homogeneous toluene 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CCC(C)(C)N2c3c(C(C)C)cccc3C)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CCC(C)(C)N2c3c(C(C)C)cccc3C)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CCC(C)(C)N2c3c(C(C)C)cccc3C)(CC)(CC) 0 1 CAAC.46 3d in Samkian2020
299 C=C (1 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 16.0 18.8 3.0 6000 U NMR, IS: TMB (1,3,5-trimethoxybenzene) batch reactor None 40 2.0 dimeric catalyst None homogeneous neat (catalyst added in CH2Cl2 solution) 5.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 - - 0 1 CAAC.47 Ru-1 in Nascimento2019 (DOI: 10.1021/jacs.9b05362)
300 C=C (8 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 39.0 51.3 20.0 40000 U NMR, IS: TMB (1,3,5-trimethoxybenzene) batch reactor None 40 2.0 dimeric catalyst None homogeneous neat (catalyst added in CH2Cl2 solution) 5.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 - - 0 1 CAAC.47 Ru-1 in Nascimento2019
301 C=C (14 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 28.0 89.3 25.0 50000 U NMR, IS: TMB (1,3,5-trimethoxybenzene) batch reactor None 40 2.0 dimeric catalyst None homogeneous neat (catalyst added in CH2Cl2 solution) 5.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 - - 0 1 CAAC.47 Ru-1 in Nascimento2019
302 C=C (28 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 18.0 44.4 8.0 16000 U NMR, IS: TMB (1,3,5-trimethoxybenzene) batch reactor None 40 2.0 dimeric catalyst None homogeneous neat (catalyst added in CH2Cl2 solution) 5.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 - - 0 1 CAAC.47 Ru-1 in Nascimento2019
303 C=C (14 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 39.0 59.0 23.0 46000 U NMR, IS: TMB (1,3,5-trimethoxybenzene) batch reactor None 40 2.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 5.0 CC(C)Oc1ccc([N+](=O)[O-])cc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 CC(C)[O+]7c1ccc([N+](=O)[O-])cc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 CC(C)Oc1ccc([N+](=O)[O-])cc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 0 1 CAAC.48 nG-C1 in Nascimento2019
304 C=C (14 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 9.0 55.6 5.0 10000 U NMR, IS: TMB (1,3,5-trimethoxybenzene) batch reactor None 40 2.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 HII-C2 in Nascimento2019
305 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 77.0 98.0 75.5 755 U GC batch reactor None 25 6.0 None None homogeneous CH2Cl2 1000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 G1 in Zimmerer2019 (DOI: 10.1039/c9gc00312f)
306 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 87.0 98.0 85.3 171 U GC batch reactor None 25 6.0 None None homogeneous CH2Cl2 5000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 G1 in Zimmerer2019
307 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 75.0 97.0 72.8 728 U GC batch reactor None 25 6.0 None None homogeneous CH2Cl2 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
308 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 95.0 96.0 91.2 182 U GC batch reactor None 25 6.0 None None homogeneous CH2Cl2 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
309 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 50.0 95.0 47.5 475 U GC batch reactor None 45 6.0 None None homogeneous scCO2 1000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 G1 in Zimmerer2019
310 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 61.0 99.0 60.4 60 U GC batch reactor None 45 6.0 None None homogeneous scCO2 10000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 G1 in Zimmerer2019
311 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 24.0 92.0 22.1 221 U GC batch reactor None 45 6.0 None None homogeneous scCO2 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
312 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 26.0 99.0 25.7 257 U GC batch reactor None 45 18.0 None None homogeneous scCO2 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
313 C=C (5 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 28.0 99.0 27.7 277 U GC batch reactor None 45 6.0 None None homogeneous scCO2 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
314 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 65.0 99.0 64.4 322 U GC batch reactor None 45 6.0 None None homogeneous scCO2 2000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
315 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 61.0 99.0 60.4 302 U GC batch reactor None 45 18.0 None None homogeneous scCO2 2000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
316 C=C (5 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 56.0 99.0 55.4 277 U GC batch reactor None 45 6.0 None None homogeneous scCO2 2000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
317 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 69.0 99.0 68.3 137 U GC batch reactor None 45 2.0 None None homogeneous scCO2 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
318 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 88.0 99.0 87.1 174 U GC batch reactor None 45 6.0 None None homogeneous scCO2 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
319 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 86.0 99.0 85.1 170 U GC batch reactor None 45 18.0 None None homogeneous scCO2 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
320 C=C (5 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 83.0 99.0 82.2 164 U GC batch reactor None 45 6.0 None None homogeneous scCO2 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
321 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 88.0 96.0 84.5 84 U GC batch reactor None 45 6.0 None None homogeneous scCO2 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
322 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 93% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC from C18:2 oil 88.0 97.0 85.4 85 U GC batch reactor None 45 18.0 None None homogeneous scCO2 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Zimmerer2019
323 C=C (20 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 89.0 76.0 67.6 13528 S1 GC, IS: tetradecane semi-batch autoclave None 70 5.0 None None homogeneous neat (catalyst added as 0.1 mL CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 Ru13 in Malecki2019 (DOI: 10.1021/acscatal.8b04783)
324 C=C (20 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 67.0 97.0 65.0 12998 S1 GC, IS: tetradecane semi-batch autoclave None 70 5.0 None None homogeneous neat (catalyst added as 0.1 mL CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4ccccc4 0 1 NHC.129 Ru8 in Malecki2019
325 C=C (20 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 59.0 98.0 57.8 11564 S1 GC, IS: tetradecane semi-batch autoclave None 70 5.0 None None homogeneous neat (catalyst added as 0.1 mL CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(CC)CC)cccc3C(CC)CC)Cc4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(CC)CC)cccc3C(CC)CC)Cc4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(CC)CC)cccc3C(CC)CC)Cc4ccccc4 0 1 NHC.130 Ru9 in Malecki2019
326 C=C (20 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 48.0 98.0 47.0 9408 S1 GC, IS: tetradecane semi-batch autoclave None 70 5.0 None None homogeneous neat (catalyst added as 0.1 mL CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(c5ccccc5)c6ccccc6)cccc3C(c7ccccc7)c8ccccc8)Cc4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(c5ccccc5)c6ccccc6)cccc3C(c7ccccc7)c8ccccc8)Cc4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(c5ccccc5)c6ccccc6)cccc3C(c7ccccc7)c8ccccc8)Cc4ccccc4 0 1 NHC.131 Ru10 in Malecki2019
327 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 57.0 93.0 53.0 1060 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 Ru-1 in Wyrebek2018 (DOI: 10.1021/acsomega.8b03119)
328 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 67.0 93.0 62.3 1246 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 Ru-2 in Wyrebek2018
329 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 52.0 98.0 51.0 1019 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 Ru-3 in Wyrebek2018
330 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 65.0 90.0 58.5 1170 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P4(CC(C)C)C5CCCC4CCC5.P6(CC(C)C)C7CCCC6CCC7 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+]4(CC(C)C)C5CCCC4CCC5)[P+]6(CC(C)C)C7CCCC6CCC7 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+]4(CC(C)C)C5CCCC4CCC5 0 1 G1-ind.3 Ru-4 in Wyrebek2018
331 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 71.0 43.0 30.5 611 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-5 in Wyrebek2018
332 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 77.0 76.0 58.5 1170 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](I)(I)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(I)(I)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(I)(I)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.006 Ru-6 in Wyrebek2018
333 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 56.0 3.0 1.7 34 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc([N+](=O)[O-])cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc([N+](=O)[O-])cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc([N+](=O)[O-])cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.007 Ru-7 in Wyrebek2018
334 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 38.0 40.0 15.2 304 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc([N+](=O)[O-])cc1C=[Ru](I)(I)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc([N+](=O)[O-])cc1[CH][Ru-2]7(I)(I)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc([N+](=O)[O-])cc1[CH]7C[CH2][Ru-]7(I)(I)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.008 Ru-8 in Wyrebek2018
335 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 79.0 70.0 55.3 1106 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(NC(=O)C(F)(F)F)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.009 Ru-9 in Wyrebek2018
336 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 59.0 73.0 43.1 861 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1C=[Ru](I)(I)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(NC(=O)C(F)(F)F)cc1[CH][Ru-2]7(I)(I)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1[CH]7C[CH2][Ru-]7(I)(I)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.010 Ru-10 in Wyrebek2018
337 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 53.0 17.0 9.0 180 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(NC(=O)OCC(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(NC(=O)OCC(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.011 Ru-11 in Wyrebek2018
338 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 56.0 15.0 8.4 168 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 Ru-12 in Wyrebek2018
339 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 80.0 72.0 57.6 1152 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.013 Ru-13 in Wyrebek2018
340 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 74.0 78.0 57.7 1154 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc([N+](=O)[O-])cc1C=[Ru](I)(I)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc([N+](=O)[O-])cc1[CH][Ru-2]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc([N+](=O)[O-])cc1[CH]7C[CH2][Ru-]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.014 Ru-14 in Wyrebek2018
341 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 77.0 66.0 50.8 1016 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(OC)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(OC)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(OC)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.015 Ru-15 in Wyrebek2018
342 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 84.0 74.0 62.2 1243 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)C(F)(F)F)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.016 Ru-16 in Wyrebek2018
343 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 70.0 89.0 62.3 1246 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1C=[Ru](I)(I)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)C(F)(F)F)cc1[CH][Ru-2]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1[CH]7C[CH2][Ru-]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.017 Ru-17 in Wyrebek2018
344 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 84.0 83.0 69.7 1394 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 Ru-18 in Wyrebek2018
345 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 42.0 99.0 41.6 832 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](I)(I)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(I)(I)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(I)(I)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.53 Ru-19 in Wyrebek2018
346 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 72.0 88.0 63.4 1267 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.18 Ru-20 in Wyrebek2018
347 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 57.0 26.0 14.8 296 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 C5CCCC5Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C5CCCC5[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C5CCCC5Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.021 Ru-21 in Wyrebek2018
348 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 59.0 21.0 12.4 248 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 C5CCCCC5Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C5CCCCC5[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C5CCCCC5Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.022 Ru-22 in Wyrebek2018
349 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 81.0 43.0 34.8 697 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CON(C)C(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.023 Ru-23 in Wyrebek2018
350 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 82.0 69.0 56.6 1132 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CON(C)C(=O)C(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.024 Ru-24 in Wyrebek2018
351 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 51.0 38.0 19.4 969 S1 GC, IS: tetradecane batch autoclave air 30 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CON(C)C(=O)C(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.024 Ru-24 in Wyrebek2018
352 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 58.0 45.0 26.1 1305 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CON(C)C(=O)C(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.024 Ru-24 in Wyrebek2018
353 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 65.0 43.0 28.0 1398 S1 GC, IS: tetradecane batch autoclave air 80 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CON(C)C(=O)C(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.024 Ru-24 in Wyrebek2018
354 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 34.0 14.0 4.8 238 S1 GC, IS: tetradecane batch autoclave air 50 1.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CON(C)C(=O)C(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.024 Ru-24 in Wyrebek2018
355 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 68.0 49.0 33.3 1666 S1 GC, IS: tetradecane batch autoclave air 50 6.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CON(C)C(=O)C(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.024 Ru-24 in Wyrebek2018
356 C=C (2 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 63.0 26.0 16.4 819 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CON(C)C(=O)C(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.024 Ru-24 in Wyrebek2018
357 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 77.0 68.0 52.4 2618 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CON(C)C(=O)C(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.024 Ru-24 in Wyrebek2018
358 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 74.0 54.0 40.0 799 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CON(C)C(=O)C(C)Oc1ccc(OC)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)[O+]7c1ccc(OC)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CON(C)C(=O)C(C)Oc1ccc(OC)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.025 Ru-25 in Wyrebek2018
359 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 17.0 22.0 3.7 75 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(C(c5ccccc5)=NN2c3ccccc3)c4ccccc4.P(C6CCCCC6)(C7CCCCC7)C8CCCCC8 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(C(c5ccccc5)=NN2c3ccccc3)c4ccccc4)[P+](C6CCCCC6)(C7CCCCC7)C8CCCCC8 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(c5ccccc5)=NN2c3ccccc3)c4ccccc4 0 1 NHC.026 Ru-26 in Wyrebek2018
360 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 39.0 38.0 14.8 296 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N4(C(COC5Cc6ccccc6C45)=NN2c3c(C)cc(C)cc3C).P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N4(C(COC5Cc6ccccc6C45)=NN2c3c(C)cc(C)cc3C))[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N4(C(COC5Cc6ccccc6C45)=NN2c3c(C)cc(C)cc3C) 0 1 NHC.027 Ru-27 in Wyrebek2018
361 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 54.0 4.0 2.2 43 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.028 Ru-28 in Wyrebek2018
362 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 40.0 23.0 9.2 184 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 O=C(C(F)(F)F)N5c1ccccc1C=[Ru]5(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n6ccccc6 O=C(C(F)(F)F)N5c1ccccc1[CH][Ru-2]5(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 O=C(C(F)(F)F)N5c1ccccc1[CH]7C[CH2][Ru-]75(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.029 Ru-29 in Wyrebek2018
363 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 81.0 49.0 39.7 794 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C.P7(CC(C)C)C8CCCC7CCC8 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C)[P+]7(CC(C)C)C8CCCC7CCC8 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.030 Ru-30 in Wyrebek2018
364 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 60.0 28.0 16.8 336 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 s1cccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 s1cccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 s1cccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.031 Ru-31 in Wyrebek2018
365 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 48.0 13.0 6.2 125 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c5ccccc5[S+]([O-])c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5ccccc5[S+]7([O-])c1ccccc1[CH][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5ccccc5[S+]([O-])c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.032 Ru-32 in Wyrebek2018
366 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 58.0 32.0 18.6 371 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 [B-](F)(F)(F)F.C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)[CH][Ru-](Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.033 Ru-33 in Wyrebek2018
367 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 64.0 33.0 21.1 422 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 O5c1ccccc1C=[Ru]5(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C6CCCCC6)(C7CCCCC7)C8CCCCC8 O5c1ccccc1[CH][Ru-2]5(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C6CCCCC6)(C7CCCCC7)C8CCCCC8 O5c1ccccc1[CH]7C[CH2][Ru-]75(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.034 Ru-34 in Wyrebek2018
368 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 38.0 17.0 6.5 129 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 N(C)(C)Cc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C [N+]7(C)(C)Cc1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C N(C)(C)Cc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.035 Ru-35 in Wyrebek2018
369 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 70.0 45.0 31.5 630 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 O5C(=O)C(C(C)C)Oc1ccccc1C=[Ru]5(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C O5C(=O)C(C(C)C)[O+]7c1ccccc1[CH][Ru-2]57(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C O5C(=O)C(C(C)C)Oc1ccccc1[CH]7C[CH2][Ru-]75(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.036 Ru-36 in Wyrebek2018
370 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 54.0 8.0 4.3 86 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(=O)COc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)COc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.037 Ru-37 in Wyrebek2018
371 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 23.0 80.0 18.4 368 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 OC(=O)C(C(C)C)Oc1ccccc1C=[Ru](I)(OC(=O)C(F)(F)F)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C OC(=O)C(C(C)C)[O+]7c1ccccc1[CH][Ru-2]7(I)(OC(=O)C(F)(F)F)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C OC(=O)C(C(C)C)Oc1ccccc1[CH]7C[CH2][Ru-]7(I)(OC(=O)C(F)(F)F)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.038 Ru-38 in Wyrebek2018
372 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 57.0 12.0 6.8 137 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 Ru-39 in Wyrebek2018
373 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 62.0 30.0 18.6 372 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(C(COC(=O)(c5c(F)c(F)c(F)c(F)c5F))CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(C(COC(=O)(c5c(F)c(F)c(F)c(F)c5F))CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(COC(=O)(c5c(F)c(F)c(F)c(F)c5F))CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.040 Ru-40 in Wyrebek2018
374 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 64.0 31.0 19.8 397 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(C(N(C)C)=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(C(N(C)C)=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(N(C)C)=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.041 Ru-41 in Wyrebek2018
375 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 66.0 38.0 25.1 502 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(C(N(C)C)=C(N(C)C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(C(N(C)C)=C(N(C)C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(N(C)C)=C(N(C)C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.042 Ru-42 in Wyrebek2018
376 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 59.0 22.0 13.0 260 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(C(N(C)C)=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(C(N(C)C)=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(N(C)C)=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.043 Ru-43 in Wyrebek2018
377 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 59.0 29.0 17.1 342 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(C(N(C)C)=C(N(C)C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(C(N(C)C)=C(N(C)C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(N(C)C)=C(N(C)C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.044 Ru-44 in Wyrebek2018
378 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 63.0 14.0 8.8 176 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.045 Ru-45 in Wyrebek2018
379 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 59.0 13.0 7.7 153 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(C)cc1C=[Ru](Cl)(Cl)=C2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.046 Ru-46 in Wyrebek2018
380 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 55.0 10.0 5.5 110 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc(OC)cc1C=[Ru](Cl)(Cl)=C2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(OC)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(OC)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.047 Ru-47 in Wyrebek2018
381 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 55.0 5.0 2.8 55 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccc([N+](=O)[O-])cc1C=[Ru](Cl)(Cl)=C2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc([N+](=O)[O-])cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc([N+](=O)[O-])cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(CN(C)C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.048 Ru-48 in Wyrebek2018
382 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 55.0 17.0 9.4 187 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(C5C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(C5=C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C5=C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.049 Ru-49 in Wyrebek2018
383 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 54.0 15.0 8.1 162 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c7ccc1c(c7)C(c8ccccc8)=CC1=[Ru](Cl)(Cl)=C2N(C5C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c7ccc1c(c7)C(c8ccccc8)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(C5=C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c7ccc1c(c7)C(c8ccccc8)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C5=C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.050 Ru-50 in Wyrebek2018
384 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 62.0 19.0 11.8 236 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(C5C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(C5=C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C5=C(C(=O)c6ccccc6C(=O)5)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.051 Ru-51 in Wyrebek2018
385 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 55.0 21.0 11.6 231 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c5cccc3)c4c(CCCCCCCC5)cccc4.P(C6CCCCC6)(C7CCCCC7)C8CCCCC8 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c5cccc3)c4c(CCCCCCCC5)cccc4)[P+](C6CCCCC6)(C7CCCCC7)C8CCCCC8 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c5cccc3)c4c(CCCCCCCC5)cccc4 0 1 NHC.052 Ru-52 in Wyrebek2018
386 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 53.0 14.0 7.4 148 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c1ccccc1C=[Ru@](Cl)(Cl)=C2N(CCN2c3c5cccc3)c4c(CCCCCCCC5)cccc4.P(C6CCCCC6)(C7CCCCC7)C8CCCCC8 c1ccccc1[CH][Ru@-2](Cl)(Cl)([C+]2N(CCN2c3c5cccc3)c4c(CCCCCCCC5)cccc4)[P+](C6CCCCC6)(C7CCCCC7)C8CCCCC8 - 0 1 NHC.053 Ru-53 in Wyrebek2018
387 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 72.0 55.0 39.6 792 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c5cccc3)c4c(CCCCCCCC5)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c5cccc3)c4c(CCCCCCCC5)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c5cccc3)c4c(CCCCCCCC5)cccc4 0 1 NHC.054 Ru-54 in Wyrebek2018
388 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 82.0 72.0 59.0 1181 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4ccccc4.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4ccccc4)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4ccccc4 0 1 NHC.055 Ru-55 in Wyrebek2018
389 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 81.0 80.0 64.8 1296 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.056 Ru-56 in Wyrebek2018
390 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 70.0 64.0 44.8 896 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(N(C)C)cccc4.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(N(C)C)cccc4)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(N(C)C)cccc4 0 1 NHC.057 Ru-57 in Wyrebek2018
391 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 68.0 75.0 51.0 1020 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4ccccc4 0 1 NHC.058 Ru-58 in Wyrebek2018
392 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 61.0 71.0 43.3 866 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.059 Ru-59 in Wyrebek2018
393 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 52.0 78.0 40.6 2028 S1 GC, IS: tetradecane batch autoclave air 30 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.059 Ru-59 in Wyrebek2018
394 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 63.0 84.0 52.9 2646 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.059 Ru-59 in Wyrebek2018
395 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 60.0 73.0 43.8 2190 S1 GC, IS: tetradecane batch autoclave air 80 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.059 Ru-59 in Wyrebek2018
396 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 50.0 22.0 11.0 550 S1 GC, IS: tetradecane batch autoclave air 50 1.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.059 Ru-59 in Wyrebek2018
397 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 62.0 78.0 48.4 2418 S1 GC, IS: tetradecane batch autoclave air 50 6.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.059 Ru-59 in Wyrebek2018
398 C=C (2 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 51.0 54.0 27.5 1377 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.059 Ru-59 in Wyrebek2018
399 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 54.0 87.0 47.0 2349 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(OC)cccc4 0 1 NHC.059 Ru-59 in Wyrebek2018
400 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 61.0 67.0 40.9 817 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4c(N(C)C)cccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(N(C)C)cccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4c(N(C)C)cccc4 0 1 NHC.060 Ru-60 in Wyrebek2018
401 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 77.0 89.0 68.5 1371 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c4ccccc4c5ccccc5c3c6ccccc6)Cc7ccccc7 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c4ccccc4c5ccccc5c3c6ccccc6)Cc7ccccc7 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c4ccccc4c5ccccc5c3c6ccccc6)Cc7ccccc7 0 1 NHC.061 Ru-61 in Wyrebek2018
402 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 39.0 78.0 30.4 608 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)Cc4cccs4 0 1 NHC.062 Ru-62 in Wyrebek2018
403 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 70.0 90.0 63.0 1260 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
404 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 58.0 91.0 52.8 2639 S1 GC, IS: tetradecane batch autoclave air 30 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
405 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 50.0 90.0 45.0 2250 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
406 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 45.0 89.0 40.1 2003 S1 GC, IS: tetradecane batch autoclave air 80 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
407 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 49.0 91.0 44.6 2230 S1 GC, IS: tetradecane batch autoclave air 50 1.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
408 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 66.0 89.0 58.7 2937 S1 GC, IS: tetradecane batch autoclave air 50 6.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
409 C=C (2 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 31.0 75.0 23.3 1163 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
410 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 73.0 97.0 70.8 3541 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
411 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 54.0 97.0 52.4 5238 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
412 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 36.0 98.0 35.3 7056 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
413 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 17.0 99.0 16.8 6732 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 25.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
414 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 72.0 97.0 69.8 3492 S1 GC, IS: tetradecane batch autoclave air 50 6.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 200.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
415 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 57.0 98.0 55.9 5586 S1 GC, IS: tetradecane batch autoclave air 50 6.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
416 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 38.0 98.0 37.2 7448 S1 GC, IS: tetradecane batch autoclave air 50 6.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
417 C=C (20 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 19.0 98.0 18.6 7448 S1 GC, IS: tetradecane batch autoclave air 50 6.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 25.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.063 Ru-63 in Wyrebek2018
418 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 42.0 99.0 41.6 832 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](I)(I)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccs4 0 1 NHC.064 Ru-64 in Wyrebek2018
419 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 95% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC from C18:2 oil 17.0 91.0 15.5 309 S1 GC, IS: tetradecane batch autoclave air 50 3.0 None None homogeneous CH2Cl2 (catalyst solution, 0.1 mL added to substrate) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccn4c5ccccc5 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccn4c5ccccc5 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)Cc4cccn4c5ccccc5 0 1 NHC.065 Ru-65 in Wyrebek2018
420 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 50.0 35.0 18.0 350 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@H](c3ccccc3)[C@H](c4ccccc4)N2CC(C)(C)C)CC(C)(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@H](c3ccccc3)[C@H](c4ccccc4)N2CC(C)(C)C)CC(C)(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@H](c3ccccc3)[C@H](c4ccccc4)N2CC(C)(C)C)CC(C)(C)C 0 1 NHC.103 4 in Ambrosio2018 (DOI: 10.1039/c8dt00619a)
421 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 28.0 37.0 10.0 207 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@H](c3ccccc3)[C@@H](c4ccccc4)N2CC(C)(C)C)CC(C)(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@H](c3ccccc3)[C@@H](c4ccccc4)N2CC(C)(C)C)CC(C)(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@H](c3ccccc3)[C@@H](c4ccccc4)N2CC(C)(C)C)CC(C)(C)C 0 1 NHC.104 5 in Ambrosio2018
422 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 25.0 32.0 8.0 160 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2C3CCCCC3)C4CCCCC4 0 1 NHC.105 6 in Ambrosio2018
423 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 49.0 20.0 10.0 196 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@H](c5ccccc5)[C@@H](c6ccccc6)N2C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@@H](c6ccccc6)N2C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@@H](c6ccccc6)N2C3CCCCC3)C4CCCCC4 0 1 NHC.106 7 in Ambrosio2018
424 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 71.0 43.0 30.0 600 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HGII in Ambrosio2018
425 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 38.0 77.0 29.0 580 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)C4CCCCC4 0 1 NHC.095 9b in Paradiso2017 (DOI: 10.1021/acs.organomet.7b00488)
426 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 63.0 58.0 36.0 720 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)C4CCCCC4 0 1 NHC.096 10b in Paradiso2017
427 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 53.0 60.0 32.0 640 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@H](c4ccccc4)[C@H](c5ccccc5)N2c3c(C(C)C)cccc3)CC(C)(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@H](c4ccccc4)[C@H](c5ccccc5)N2c3c(C(C)C)cccc3)CC(C)(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@H](c4ccccc4)[C@H](c5ccccc5)N2c3c(C(C)C)cccc3)CC(C)(C)C 0 1 NHC.097 11a in Paradiso2017
428 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 70.0 64.0 45.0 900 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@@H](c4ccccc4)[C@H](c5ccccc5)N2c3c(C(C)C)cccc3)CC(C)(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@@H](c4ccccc4)[C@H](c5ccccc5)N2c3c(C(C)C)cccc3)CC(C)(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@@H](c4ccccc4)[C@H](c5ccccc5)N2c3c(C(C)C)cccc3)CC(C)(C)C 0 1 NHC.098 12a in Paradiso2017
429 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 53.0 43.0 23.0 460 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)CC(C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)CC(C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)CC(C)(C)c4ccccc4 0 1 NHC.099 11b in Paradiso2017
430 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 71.0 57.0 40.0 800 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)CC(C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)CC(C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C(C)C)cccc3)CC(C)(C)c4ccccc4 0 1 NHC.100 12b in Paradiso2017
431 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 75.0 81.0 61.0 1220 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 0 1 NHC.101 11c in Paradiso2017
432 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 81.0 83.0 67.0 1340 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 0 1 NHC.102 12c in Paradiso2017
433 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 85.0 83.0 70.0 1400 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 BerEt in Paradiso2017
434 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 71.0 43.0 30.0 600 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HGII in Paradiso2017
435 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 48.0 86.0 41.0 4100 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 0 1 NHC.102 12c in Paradiso2017
436 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 49.0 90.0 44.0 4400 S1 GC, IS: dodecane batch autoclave nitrogen 50 2.0 None None homogeneous neat (catalyst added in toluene solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 0 1 NHC.102 12c in Paradiso2017
437 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 39.0 88.0 34.0 3400 S1 GC, IS: dodecane batch autoclave nitrogen 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 0 1 NHC.102 12c in Paradiso2017
438 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 (major, n.r.%) CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 18.0 83.0 15.0 7500 S1 GC, IS: dodecane batch autoclave nitrogen 50 3.0 None None homogeneous neat (catalyst added in toluene solution) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N([C@@H](c5ccccc5)[C@H](c6ccccc6)N2c3c(C)cc(C)cc3C)C4CCCCC4 0 1 NHC.102 12c in Paradiso2017
439 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 65.0 74.0 49.0 637 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.08 250W microwave heating None homogeneous neat (catalyst added as solid) 1000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 G1 in Ullah2017 (DOI : 10.1002/cssc.201601824)
440 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 70.0 90.0 1170 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.08 250W microwave heating None homogeneous neat (catalyst added as solid) 1000.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Ullah2017
441 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 64.0 88.0 63.0 819 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.08 250W microwave heating None homogeneous neat (catalyst added as solid) 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Ullah2017
442 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 95.0 32.0 57.0 1482 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.01 250W microwave heating None homogeneous neat (catalyst added as solid) 500.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 G2 in Ullah2017
443 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 65.0 84.0 2184 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.01 250W microwave heating None homogeneous neat (catalyst added as solid) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
444 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 60.0 70.0 9100 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
445 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 95.0 52.0 66.0 17160 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
446 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 69.0 42.0 33.0 21450 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 20.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
447 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 46.0 62.0 806 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 40 0.05 250W microwave heating None homogeneous neat (catalyst added as solid) 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
448 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 66.0 88.0 1144 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
449 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 64.0 85.0 1105 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 60 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
450 C=C (6.9 bar, 99.9%) COME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 69.0 89.0 1157 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 80 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
451 C=C (6.9 bar, 99.9%) WOME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 63.0 75.0 825 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
452 C=C (6.9 bar, 99.9%) WOME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 57.0 70.0 1540 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
453 C=C (6.9 bar, 99.9%) WOME (C18:1/2/3) C18:1 (major, n.r.%) mixture esters/olefins None None None None 96.0 59.0 72.0 15840 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
454 C=C (6.9 bar, 99.9%) canola oil (TAG) C18:1 (major, n.r.%) mixture esters/olefins None None None None 95.0 4.0 34.0 2652 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
455 C=C (6.9 bar, 99.9%) canola oil (TAG) C18:1 (major, n.r.%) mixture esters/olefins None None None None 94.0 19.0 49.0 19110 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
456 C=C (6.9 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 94.0 19.0 34.0 6800 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
457 C=C (6.9 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 94.0 36.0 40.0 8000 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
458 C=C (6.9 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 94.0 65.0 72.0 7200 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
459 C=C (6.9 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 92.0 56.0 75.0 7500 O GC, IS: methyl palmitate and/or methyl heptadecanoate sealed vial nitrogen 50 0.02 250W microwave heating None homogeneous neat (catalyst added as solid) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG2 in Ullah2017
460 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 61.0 91.0 56.0 56000 S1 GC, IS: methyl stearate (residual) batch reactor None 40 2.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 12g in Gawin2017 (DOI: 10.1002/anie.201609009)
461 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 92.0 47.0 94000 S1 GC, IS: methyl stearate (residual) batch reactor None 40 2.0 None None homogeneous neat (catalyst added in toluene solution) 5.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 12g in Gawin2017
462 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 1.0 0.0 0.0 0 S1 GC, IS: methyl stearate (residual) batch reactor None 60 4.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)(C))=C6C(CC(C)(C)N6c7c(CC)cccc7CC)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)(C))[C+]6C(CC(C)(C)N6c7c(CC)cccc7CC)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)(C) 0 1 CAAC.01 15a in Gawin2017
463 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 3.0 0.0 0.0 0 S1 GC, IS: methyl stearate (residual) batch reactor None 60 4.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(C)cc(C)cc5C)(C)(C))=C6C(CC(C)(C)N6c7c(C)cc(C)cc7C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(C)cc(C)cc5C)(C)(C))[C+]6C(CC(C)(C)N6c7c(C)cc(C)cc7C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(C)cc(C)cc5C)(C)(C) 0 1 CAAC.02 15b in Gawin2017
464 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 21.0 92.0 19.0 19000 S1 GC, IS: methyl stearate (residual) batch reactor None 60 4.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(C)cc(C)cc5C)(C)c8ccccc8)=C6C(CC(C)(C)N6c7c(C)cc(C)cc7C)(C)c9ccccc9 c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(C)cc(C)cc5C)(C)c8ccccc8)[C+]6C(CC(C)(C)N6c7c(C)cc(C)cc7C)(C)c9ccccc9 c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(C)cc(C)cc5C)(C)c8ccccc8 0 1 CAAC.03 15c in Gawin2017
465 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 1.0 0.0 0.0 0 S1 GC, IS: methyl stearate (residual) batch reactor None 60 4.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(CC)cccc5C)(C)(C))=C6C(CC(C)(C)N6c7c(CC)cccc7C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(CC)cccc5C)(C)(C))[C+]6C(CC(C)(C)N6c7c(CC)cccc7C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(CC)cccc5C)(C)(C) 0 1 CAAC.04 15d in Gawin2017
466 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 57.0 89.0 51.0 51000 S1 GC, IS: methyl stearate (residual) batch reactor None 60 4.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(CC)cccc5C)(C)c8ccccc8)=C6C(CC(C)(C)N6c7c(CC)cccc7C)(C)c9ccccc9 c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(CC)cccc5C)(C)c8ccccc8)[C+]6C(CC(C)(C)N6c7c(CC)cccc7C)(C)c9ccccc9 c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(CC)cccc5C)(C)c8ccccc8 0 1 CAAC.05 15e in Gawin2017
467 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 60.0 88.0 53.0 53000 S1 GC, IS: methyl stearate (residual) batch reactor None 50 4.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)c8ccccc8)=C6C(CC(C)(C)N6c7c(CC)cccc7CC)(C)c9ccccc9 c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)c8ccccc8)[C+]6C(CC(C)(C)N6c7c(CC)cccc7CC)(C)c9ccccc9 c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)c8ccccc8 0 1 CAAC.06 15f in Gawin2017
468 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 41.0 91.0 37.0 74000 S1 GC, IS: methyl stearate (residual) batch reactor None 50 4.0 None None homogeneous neat (catalyst added in toluene solution) 5.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)c8ccccc8)=C6C(CC(C)(C)N6c7c(CC)cccc7CC)(C)c9ccccc9 c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)c8ccccc8)[C+]6C(CC(C)(C)N6c7c(CC)cccc7CC)(C)c9ccccc9 c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(CC)cccc5CC)(C)c8ccccc8 0 1 CAAC.06 15f in Gawin2017
469 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 69.0 87.0 60.0 60000 S1 GC, IS: methyl stearate (residual) batch reactor None 55 4.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(C(C)C)cccc5C)(C)(C))=C6C(CC(C)(C)N6c7c(C(C)C)cccc7C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(C(C)C)cccc5C)(C)(C))[C+]6C(CC(C)(C)N6c7c(C(C)C)cccc7C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(C(C)C)cccc5C)(C)(C) 0 1 CAAC.07 15g in Gawin2017
470 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 48.0 90.0 43.0 86000 S1 GC, IS: methyl stearate (residual) batch reactor None 60 4.0 None None homogeneous neat (catalyst added in toluene solution) 5.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c(C(C)C)cccc5C)(C)(C))=C6C(CC(C)(C)N6c7c(C(C)C)cccc7C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c(C(C)C)cccc5C)(C)(C))[C+]6C(CC(C)(C)N6c7c(C(C)C)cccc7C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c(C(C)C)cccc5C)(C)(C) 0 1 CAAC.07 15g in Gawin2017
471 C=C (10 bar, 99.99%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 37.0 91.0 34.0 34000 S1 GC, IS: methyl stearate (residual) batch reactor None 60 4.0 None None homogeneous neat (catalyst added in toluene solution) 10.0 c3ccc1c(c3)C(c2ccccc2)=CC1=[Ru](Cl)(Cl)(=C4C(CC(C)(C)N4c5c6cc(C(C)C)ccc6ccc5C(C)C)(C)(C))=C7C(CC(C)(C)N7c8c9cc(C(C)C)ccc9ccc8C(C)C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]1[Ru-2](Cl)(Cl)([C+]4C(CC(C)(C)N4c5c6cc(C(C)C)ccc6ccc5C(C)C)(C)(C))[C+]7C(CC(C)(C)N7c8c9cc(C(C)C)ccc9ccc8C(C)C)(C)(C) c3ccc1c(c3)C(c2ccccc2)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]4C(CC(C)(C)N4c5c6cc(C(C)C)ccc6ccc5C(C)C)(C)(C) 0 1 CAAC.08 15h in Gawin2017
472 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 99% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 97.0 46.0 60.0 5998 S3 GC semi-batch autoclave None 60 1.0 None None homogeneous toluene 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 1 in Engl2016 (DOI: 10.1021/acs.organomet.6b00028)
473 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 99% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 95.0 43.0 64.0 32018 S3 GC semi-batch autoclave None 60 1.0 None None homogeneous toluene 20.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 1 in Engl2016
474 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 99% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 44.0 40.0 19.0 1901 S3 GC semi-batch autoclave None 60 1.0 None None homogeneous toluene 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(c4ccccc4N2c3ccccc3)C(F)(F)F.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(c4ccccc4N2c3ccccc3)C(F)(F)F)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c4ccccc4N2c3ccccc3)C(F)(F)F 0 1 NHC.090 6a in Engl2016
475 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 99% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 57.0 80.0 48.0 4778 S3 GC semi-batch autoclave None 60 1.0 None None homogeneous toluene 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(c4ccccc4N2c3ccc(C(F)(F)F)cc3)C(F)(F)F.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(c4ccccc4N2c3ccc(C(F)(F)F)cc3)C(F)(F)F)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c4ccccc4N2c3ccc(C(F)(F)F)cc3)C(F)(F)F 0 1 NHC.091 6b in Engl2016
476 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 99% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 74.0 90.0 69.0 6860 S3 GC semi-batch autoclave None 60 1.0 None None homogeneous toluene 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(c4ccccc4N2c3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(F)(F)F.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(c4ccccc4N2c3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(F)(F)F)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c4ccccc4N2c3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(F)(F)F 0 1 NHC.092 6c in Engl2016
477 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 99% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 56.0 75.0 43.0 21312 S3 GC semi-batch autoclave None 60 1.0 None None homogeneous toluene 20.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(c4ccccc4N2c3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(F)(F)F.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(c4ccccc4N2c3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(F)(F)F)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c4ccccc4N2c3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(F)(F)F 0 1 NHC.092 6c in Engl2016
478 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 99% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 60.0 89.0 55.0 5516 S3 GC semi-batch autoclave None 60 1.0 None None homogeneous toluene 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(c3ccccc3N2CCCC)C(F)(F)F.P(C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(c3ccccc3N2CCCC)C(F)(F)F)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c3ccccc3N2CCCC)C(F)(F)F 0 1 NHC.093 6d in Engl2016
479 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OCC C18:1 99% CCOC(=O)CCCCCCCC=C CCCCCCCCC=C CCOC(=O)CCCCCCCC=CCCCCCCCC(=O)OCC CCCCCCCCC=CCCCCCCCC None 47.0 26.0 17.0 1694 S3 GC semi-batch autoclave None 60 1.0 None None homogeneous toluene 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(c4ccccc4N2c3ccc(C(F)(F)F)cc3)C(C)C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(c4ccccc4N2c3ccc(C(F)(F)F)cc3)C(C)C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(c4ccccc4N2c3ccc(C(F)(F)F)cc3)C(C)C 0 1 NHC.094 7 in Engl2016
480 C=C (0.125 bar, 95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 76.0 69.0 52.0 5 S3 GC, IS: n-dodecane batch reactor nitrogen 40 None None HG2/SiO2, 10 wt% heterogeneous cyclohexane 100000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG in Nieres2016 (DOI: 10.1039/c6cy01214k)
481 C=C (0.2 bar, 95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 78.0 73.0 57.0 6 S3 GC, IS: n-dodecane batch reactor nitrogen 40 None None HG2/SiO2, 10 wt% heterogeneous cyclohexane 100000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG in Nieres2016
482 C=C (0.25 bar, 95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 82.0 77.0 63.0 6 S3 GC, IS: n-dodecane batch reactor nitrogen 40 None None HG2/SiO2, 10 wt% heterogeneous cyclohexane 100000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG in Nieres2016
483 C=C (0.3 bar, 95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 78.0 73.0 57.0 6 S3 GC, IS: n-dodecane batch reactor nitrogen 40 None None HG2/SiO2, 10 wt% heterogeneous cyclohexane 100000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG in Nieres2016
484 C=C (0.375 bar, 95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 71.0 63.0 45.0 5 S3 GC, IS: n-dodecane batch reactor nitrogen 40 None None HG2/SiO2, 10 wt% heterogeneous cyclohexane 100000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG in Nieres2016
485 C=C (0.25 bar, 95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 79.0 72.0 57.0 6 S3 GC, IS: n-dodecane batch reactor nitrogen 60 None None HG2/SiO2, 10 wt% heterogeneous cyclohexane 100000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG in Nieres2016
486 C=C (0.25 bar, 95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 75.0 72.0 54.0 5 S3 GC, IS: n-dodecane batch reactor nitrogen 75 None None HG2/SiO2, 10 wt% heterogeneous cyclohexane 100000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 HG in Nieres2016
487 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 37.0 86.0 32.0 110000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3C)(C)(C) 0 1 CAAC.09 9 in Marx2015 (DOI: 10.1002/anie.201410797)
488 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 42.0 88.0 37.0 120000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 10 in Marx2015
489 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.0 92.0 54.0 180000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 11 in Marx2015
490 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None None None 53.0 180000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 11 in Marx2015
491 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None None None 48.0 240000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 2.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 11 in Marx2015
492 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None None None 49.0 245000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 2.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 11 in Marx2015
493 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None None None 13.0 130000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 11 in Marx2015
494 C=C (10 bar, 99.995%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None None None 34.0 340000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 1.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)(C) 0 1 CAAC.11 11 in Marx2015
495 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 18.0 94.0 17.0 57000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)(C)C)cccc3C)(C)(C) 0 1 CAAC.12 12 in Marx2015
496 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 97.0 18.0 60000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) 0 1 CAAC.13 13 in Marx2015
497 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 22.0 63.0 14.0 47000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3)(CC)(CC) 0 1 CAAC.14 14 in Marx2015
498 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 26.0 86.0 22.0 73000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C)cc(C)cc3C)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C)cc(C)cc3C)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C)cc(C)cc3C)(CC)(CC) 0 1 CAAC.15 15 in Marx2015
499 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 42.0 92.0 39.0 130000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(CC)(CC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(CC)(CC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(CC)(CC) 0 1 CAAC.16 16 in Marx2015
500 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 78.0 14.0 47000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C)cc(C)cc3C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C)cc(C)cc3C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C)cc(C)cc3C)CCCCC4 0 1 CAAC.17 17 in Marx2015
501 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 13.0 97.0 13.0 43000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.18 18 in Marx2015
502 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 16.0 97.0 15.0 50000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(CCC) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(CCC) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(CCC) 0 1 CAAC.19 19 in Marx2015
503 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 5.0 0.0 0.0 0 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(CC)cccc3CC)C5CC6CC(C5)CC4C6 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(CC)cccc3CC)C5CC6CC(C5)CC4C6 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(CC)cccc3CC)C5CC6CC(C5)CC4C6 0 1 CAAC.20 20 in Marx2015
504 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 41.0 83.0 34.0 110000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C)cc(C)cc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C)cc(C)cc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C)cc(C)cc3C)(C)c4ccccc4 0 1 CAAC.21 21 in Marx2015
505 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 46.0 85.0 39.0 130000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3C)(C)c4ccccc4 0 1 CAAC.22 22 in Marx2015
506 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 48.0 88.0 43.0 140000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)c4ccccc4 0 1 CAAC.23 23 in Marx2015
507 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 57.0 94.0 54.0 180000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C)(C)c4ccccc4 0 1 CAAC.24 24 in Marx2015
508 C=C (10 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 47.0 98.0 46.0 150000 S1 GC, IS: dodecane batch reactor None 40 3.0 None None homogeneous neat (catalyst added in toluene solution) 3.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)c4ccccc4 0 1 CAAC.25 25 in Marx2015
509 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 95.0 94.0 89.3 1786 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014 (DOI: 10.1039/c4gc00111g)
510 None Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 43.0 81.0 34.8 697 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
511 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 96.0 93.0 89.3 1786 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
512 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 84.0 87.0 73.1 1462 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous toluene 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
513 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 90.0 91.0 81.9 1638 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous CH2Cl2 500.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 G1 in Julis2014
514 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 91.0 90.0 81.9 1638 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 G1 in Julis2014
515 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 57.0 19.0 10.8 217 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 M2 in Julis2014
516 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 61.0 34.0 20.7 415 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 M2 in Julis2014
517 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 84.0 68.0 57.1 1142 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 M2 in Julis2014
518 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 26.0 43.0 11.2 224 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(c7ccccc7)(c8ccccc8)c9ccccc9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](c7ccccc7)(c8ccccc8)c9ccccc9 - 0 1 NHC.077 M20 in Julis2014
519 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 83.0 54.0 44.8 896 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(c7ccccc7)(c8ccccc8)c9ccccc9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](c7ccccc7)(c8ccccc8)c9ccccc9 - 0 1 NHC.077 M20 in Julis2014
520 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 87.0 49.0 42.6 853 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(c7ccccc7)(c8ccccc8)c9ccccc9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](c7ccccc7)(c8ccccc8)c9ccccc9 - 0 1 NHC.077 M20 in Julis2014
521 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 67.0 46.0 30.8 616 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.028 M31 in Julis2014
522 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 83.0 53.0 44.0 880 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.028 M31 in Julis2014
523 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 87.0 59.0 51.3 1027 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.028 M31 in Julis2014
524 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 61.0 9.0 5.5 110 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru@](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(OC(C)C)(OC(C)C)OC(C)C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru@-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](OC(C)C)(OC(C)C)OC(C)C - 0 1 NHC.078 Caz-1 in Julis2014
525 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 58.0 22.0 12.8 255 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru@](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(OC(C)C)(OC(C)C)OC(C)C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru@-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](OC(C)C)(OC(C)C)OC(C)C - 0 1 NHC.078 Caz-1 in Julis2014
526 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 92.0 75.0 69.0 1380 O GC, IS: n-tetradecane batch reactor nitrogen 90 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru@](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(OC(C)C)(OC(C)C)OC(C)C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru@-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](OC(C)C)(OC(C)C)OC(C)C - 0 1 NHC.078 Caz-1 in Julis2014
527 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 82.0 50.0 41.0 820 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
528 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 93.0 16.0 14.9 298 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
529 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 90.0 22.0 19.8 396 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
530 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 88.0 23.0 20.2 405 O GC, IS: n-tetradecane batch reactor nitrogen 20 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)COc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)COc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.037 M52 in Julis2014
531 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 95.0 24.0 22.8 456 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)COc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)COc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.037 M52 in Julis2014
532 C=C (8 bar) Cardanol (C15:0/1/2/3) C15:0 5%, C15:1 38%, C15:2 20%, C15:3 38% Oc1cc(CCCCCCCC=C)ccc1 Oc1cc(CCCCCCC/C=C\CC=C)ccc1 None None None 89.0 22.0 19.6 392 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)COc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)COc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.037 M52 in Julis2014
533 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 0.0 0.0 0.0 0 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
534 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 64.0 55.0 35.2 704 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
535 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 63.0 46.0 29.0 580 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 1,4-hexadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
536 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 31.0 47.0 14.6 291 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 1,5-cyclooctadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
537 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 69.0 46.0 31.7 635 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 1,7-octadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
538 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc2 CCCCCCC=C None None None 28.0 13.0 3.6 72 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru@](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(OC(C)C)(OC(C)C)OC(C)C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru@-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](OC(C)C)(OC(C)C)OC(C)C - 0 1 NHC.078 Caz-1 in Julis2014
539 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc3 CCCCCCC=C None None None 78.0 11.0 8.6 172 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru@](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(OC(C)C)(OC(C)C)OC(C)C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru@-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](OC(C)C)(OC(C)C)OC(C)C - 0 1 NHC.078 Caz-1 in Julis2014
540 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc4 CCCCCCC=C None None None 72.0 9.0 6.5 130 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
541 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc5 CCCCCCC=C None None None 72.0 7.0 5.0 100 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
542 C=C (8 bar) Oc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) Oc1cc(CCCCCCCC=C)ccc6 CCCCCCC=C None None None 64.0 2.0 1.3 26 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
543 C=C (8 bar) COc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) COc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 53.0 50.0 26.5 530 O GC, IS: n-tetradecane batch reactor nitrogen 25 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
544 C=C (8 bar) COc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) COc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 56.0 53.0 29.7 594 O GC, IS: n-tetradecane batch reactor nitrogen 25 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
545 C=C (8 bar) COc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) COc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 71.0 6.0 4.3 85 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 None None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru@](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(OC(C)C)(OC(C)C)OC(C)C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru@-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](OC(C)C)(OC(C)C)OC(C)C - 0 1 NHC.078 Caz-1 in Julis2014
546 C=C (8 bar) COc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) COc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 80.0 8.0 6.4 128 O GC, IS: n-tetradecane batch reactor nitrogen 70 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru@](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(OC(C)C)(OC(C)C)OC(C)C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru@-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](OC(C)C)(OC(C)C)OC(C)C - 0 1 NHC.078 Caz-1 in Julis2014
547 C=C (8 bar) COc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) COc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 77.0 2.0 1.5 31 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 None None homogeneous CH2Cl2 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
548 C=C (8 bar) COc1cc(CCCCCCC/C=C\CCCCCC)ccc1 C15:1 (major, n.r.%) COc1cc(CCCCCCCC=C)ccc1 CCCCCCC=C None None None 86.0 3.0 2.6 52 O GC, IS: n-tetradecane batch reactor nitrogen 40 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
549 C=C (8 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C None None None 47.0 89.0 41.8 837 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
550 C=C (8 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 (major, n.r.%) COC(=O)CCCCCCCC=C CCCCCCCCC=C None None None 76.0 94.0 71.4 1429 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
551 C=C (8 bar) CCCCCCCC/C=C\CCCCCCCC(=O)Oc1cc(O)ccc1 C18:1 (major, n.r.%) c1ccc(O)cc1OC(=O)CCCCCCCC=C CCCCCCCCC=C None None None 7.0 62.0 4.3 87 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
552 C=C (8 bar) CCCCCCCC/C=C\CCCCCCCC(=O)Oc1cc(O)ccc1 C18:1 (major, n.r.%) c1ccc(O)cc1OC(=O)CCCCCCCC=C CCCCCCCCC=C None None None 13.0 57.0 7.4 148 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
553 C=C (8 bar) CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC C18:2 50%, C18:3 50% COC(=O)CCCCCCCC=C None None None None 0.0 0.0 0.0 0 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
554 C=C (8 bar) CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC C18:2 50%, C18:3 50% COC(=O)CCCCCCCC=C None None None None 0.0 0.0 0.0 0 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
555 C=C (8 bar) CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)Oc1cc(O)ccc1 C18:3 (major, n.r.%) c1ccc(O)cc1OC(=O)CCCCCCCC=C None None None None 36.0 75.0 27.0 540 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 None None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
556 C=C (8 bar) CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)Oc1cc(O)ccc1 C18:3 (major, n.r.%) c1ccc(O)cc1OC(=O)CCCCCCCC=C None None None None 5.0 0.0 0.0 0 O GC, IS: n-tetradecane batch reactor nitrogen None 6.0 1,4-cyclohexadiene added None homogeneous CH2Cl2 500.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 M1 in Julis2014
557 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 93.0 93.0 86.5 86 O GC, IS: n-dodecane batch reactor nitrogen 25 16.0 None None homogeneous CH2Cl2 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Julis2014
558 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 17.0 13.0 2.2 2 O GC, IS: n-dodecane batch reactor nitrogen 25 16.0 None None homogeneous CH2Cl2 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.028 M31 in Julis2014
559 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 30.0 18.0 5.4 5 O GC, IS: n-dodecane batch reactor nitrogen 25 16.0 None None homogeneous CH2Cl2 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Oc7ccc([N+](=O)[O-])cc7C=Nc8ccc(C)cc8)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2]9(Cl)(Oc7ccc([N+](=O)[O-])cc7C=[N+]9c8ccc(C)cc8)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Oc7ccc([N+](=O)[O-])cc7C=Nc8ccc(C)cc8)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.079 M41 in Julis2014
560 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 96.0 36.0 34.6 35 O GC, IS: n-dodecane batch reactor nitrogen 25 16.0 None None homogeneous CH2Cl2 10000.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
561 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 90.0 37.0 33.3 33 O GC, IS: n-dodecane batch reactor nitrogen 25 16.0 None None homogeneous CH2Cl2 10000.0 CC(C)Oc1ccc(NC(=O)C(=O)OCC)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(NC(=O)C(=O)OCC)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(NC(=O)C(=O)OCC)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.080 M74 in Julis2014
562 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 74.0 57.0 42.2 42 O GC, IS: n-dodecane batch reactor nitrogen 60 16.0 None None homogeneous THF 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Julis2014
563 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 88.0 16.0 14.1 14 O GC, IS: n-dodecane batch reactor nitrogen 60 16.0 None None homogeneous THF 10000.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 M51 in Julis2014
564 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 56.0 11.0 6.2 6 O GC, IS: n-dodecane batch reactor nitrogen 60 16.0 None None homogeneous THF 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.028 M31 in Julis2014
565 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 44.0 19.0 8.4 8 O GC, IS: n-dodecane batch reactor nitrogen 60 16.0 None None homogeneous THF 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Oc7ccc([N+](=O)[O-])cc7C=Nc8ccc(C)cc8)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2]9(Cl)(Oc7ccc([N+](=O)[O-])cc7C=[N+]9c8ccc(C)cc8)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Oc7ccc([N+](=O)[O-])cc7C=Nc8ccc(C)cc8)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.079 M41 in Julis2014
566 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 93.0 7.0 6.5 7 O GC, IS: n-dodecane batch reactor nitrogen 60 16.0 None None homogeneous THF 10000.0 CC(C)Oc1ccc(NC(=O)C(=O)OCC)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(NC(=O)C(=O)OCC)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(NC(=O)C(=O)OCC)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.080 M74 in Julis2014
567 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 98.0 92.0 90.2 180 O GC, IS: n-dodecane batch reactor nitrogen 25 6.0 None None homogeneous CH2Cl2 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Julis2014
568 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 92.0 93.0 85.6 856 O GC, IS: n-dodecane batch reactor nitrogen 25 6.0 None None homogeneous CH2Cl2 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Julis2014
569 C=C (8 bar) Anacardic acid methyl ester (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) COc1c(C(=O)OC)c(CCCCCCCC=C)ccc1 None None None None 78.0 93.0 72.5 1451 O GC, IS: n-dodecane batch reactor nitrogen 25 6.0 None None homogeneous CH2Cl2 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 HG1 in Julis2014
570 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 70.0 65.7 46.0 46 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 10000.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 Ru-1 in Baader2014 (DOI: 10.1039/c4gc01269k)
571 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 83.0 94.0 78.0 78 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 10000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 Ru-2 in Baader2014
572 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 94.0 97.9 92.0 92 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 Ru-3 in Baader2014
573 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 83.0 92.8 77.0 77 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 10000.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 Ru-4 in Baader2014
574 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 82.0 25.6 21.0 21 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-5 in Baader2014
575 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 87.0 0.0 0.0 0 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.028 Ru-6 in Baader2014
576 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 56.0 83.9 47.0 47 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Oc7ccc([N+](=O)[O-])cc7C=Nc8ccc(C)cc8)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2]9(Cl)(Oc7ccc([N+](=O)[O-])cc7C=[N+]9c8ccc(C)cc8)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Oc7ccc([N+](=O)[O-])cc7C=Nc8ccc(C)cc8)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.079 Ru-7 in Baader2014
577 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 81.0 87.7 71.0 142 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 Ru-3 in Baader2014
578 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 76.0 85.5 65.0 650 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 Ru-3 in Baader2014
579 C=C (10 bar, 99.9%) Anacardic acids (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) Oc1c(C(=O)O)c(CCCCCCCC=C)ccc1 None None None None 71.0 85.9 61.0 1220 O GC, IS: n-hexadecane batch autoclave None 23 16.0 None None homogeneous CH2Cl2 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 Ru-3 in Baader2014
580 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 94.0 96.0 90.0 47 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None None homogeneous toluene 19149.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 GII in Shinde2014 (DOI: 10.1016/j.apcata.2014.03.036)
581 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 78.0 91.0 71.0 39 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None G2/SBA-15, 0.30 wt% heterogeneous toluene 18205.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 GII in Shinde2014
582 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 67.0 89.0 60.0 67 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None G2/SBA-15, 0.30 wt% heterogeneous toluene 8955.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 GII in Shinde2014
583 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 65.0 86.0 56.0 163 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None G2/SBA-15, 0.30 wt% heterogeneous toluene 3436.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 GII in Shinde2014
584 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 55.0 84.0 46.0 275 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None G2/SBA-15, 0.30 wt% heterogeneous toluene 1673.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 GII in Shinde2014
585 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 33.0 79.0 26.0 330 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None G2/SBA-15, 0.30 wt% heterogeneous toluene 788.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 GII in Shinde2014
586 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 96.0 96.0 92.0 48 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None None homogeneous toluene 19167.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 ZC in Shinde2014
587 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 93.0 96.0 89.0 47 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None ZC/SBA-15, 0.93 wt% heterogeneous toluene 18936.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 ZC in Shinde2014
588 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 91.0 95.0 86.0 91 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None ZC/SBA-15, 0.93 wt% heterogeneous toluene 9451.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 ZC in Shinde2014
589 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 88.0 92.0 81.0 220 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None ZC/SBA-15, 0.93 wt% heterogeneous toluene 3682.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 ZC in Shinde2014
590 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 81.0 90.0 73.0 405 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None ZC/SBA-15, 0.93 wt% heterogeneous toluene 1802.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 ZC in Shinde2014
591 C=C (3 bar, 99.96%) Cardanol (C15:0/1/2/3) C15:0/1/2/3 (n.r.%) (cardanol 99%) Oc1cc(CCCCCCCC=C)ccc1 None None None None 63.0 89.0 56.0 630 O HPLC, IS: n-nonane semi-batch autoclave argon 60 2.0 None ZC/SBA-15, 0.93 wt% heterogeneous toluene 889.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 ZC in Shinde2014
592 C=C (8 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 54.0 13.0 7.0 72 S3 GC, IS: propylbenzene batch reactor None 30 24.0 None None homogeneous neat 1000.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 12 in Aydos2014 (DOI: 10.1016/j.catcom.2014.04.020)
593 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.0 38.0 21.0 206 S3 GC, IS: propylbenzene batch reactor None 30 24.0 None None homogeneous neat 1000.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 12 in Aydos2014
594 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 39.0 96.0 38.0 377 S3 GC, IS: propylbenzene batch reactor None 30 24.0 None None homogeneous neat 1000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 11 in Aydos2014
595 C=C (4 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 31.0 98.0 30.0 304 S3 GC, IS: propylbenzene batch reactor None 30 24.0 None None homogeneous neat 1000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 11 in Aydos2014
596 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 25.0 93.0 23.0 2677 S3 GC, IS: propylbenzene batch reactor None 30 24.0 None None homogeneous neat 85.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 11 in Aydos2014
597 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 16.0 95.0 16.0 3284 S3 GC, IS: propylbenzene batch reactor None 30 24.0 None None homogeneous neat 45.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 11 in Aydos2014
598 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 75.0 31.0 23.0 233 S3 GC, IS: propylbenzene batch reactor None 30 24.0 None None homogeneous neat 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 10 in Aydos2014
599 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 53.0 97.0 51.0 508 S3 GC, IS: propylbenzene batch reactor None 30 24.0 None None homogeneous neat 1000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 9 in Aydos2014
600 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 49.0 26.0 13.0 128 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.5g) None homogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.087 14 in Aydos2014
601 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 40.0 23.0 9.0 89 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/NTf2 (0.5g) None homogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.087 14 in Aydos2014
602 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 50.0 25.0 12.0 126 S3 GC, IS: propylbenzene batch reactor None 30 24.0 iPMI/PF6 (0.5g) None homogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.087 14 in Aydos2014
603 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 62.0 46.0 29.0 286 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.5g) None homogeneous toluene 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.087 14 in Aydos2014
604 C=C (30 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 57.0 42.0 24.0 239 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.5g) None homogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.087 14 in Aydos2014
605 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 12.0 96.0 12.0 117 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.5g) None homogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
606 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 5.0 96.0 5.0 1045 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.5g) None homogeneous neat 45.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
607 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 10.0 91.0 9.0 89 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.2g) on Celite heterogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
608 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 11.0 92.0 10.0 102 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.2g) on alumina heterogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
609 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 20.0 91.0 18.0 181 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.2g) on silica heterogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
610 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 42.0 90.0 38.0 381 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.46g) on silica heterogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
611 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 43.0 90.0 39.0 387 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.69g) on silica heterogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
612 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 52.0 93.0 49.0 491 S3 GC, IS: propylbenzene batch reactor None 30 24.0 iPMI/PF6 (0.4g) on silica heterogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
613 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 11.0 94.0 10.0 2350 S3 GC, IS: propylbenzene batch reactor None 30 24.0 iPMI/PF6 (0.4g) on silica heterogeneous neat 45.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 1 1 NHC.086 13 in Aydos2014
614 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 84.0 44.0 37.0 369 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.2g) on silica heterogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.087 14 in Aydos2014
615 C=C (30 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 82.0 43.0 35.0 353 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.2g) on silica heterogeneous neat 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.087 14 in Aydos2014
616 C=C (20 bar, 99.5%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 95% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 42.0 19.0 190 S3 GC, IS: propylbenzene batch reactor None 30 24.0 BMI/PF6 (0.2g) on silica heterogeneous toluene 1000.0 F[P-](F)(F)(F)(F)F.c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C c5c[n+](C)c(C)n5C(C)CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.087 14 in Aydos2014
617 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 45.0 0.0 0.0 0 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 Ru-1 in Bidange2014 (DOI: 10.1002/ejlt.201400184)
618 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 80.0 91.0 72.8 29 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 Ru-2 in Bidange2014
619 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 45.0 0.0 0.0 0 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 Ru-3 in Bidange2014
620 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 82.0 95.0 77.9 31 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 c1(OC(C)C)cc(OC(C)C)c2c(c1)C(c3cc(OC(C)C)cc(OC(C)C)c3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1(OC(C)C)cc([O+]7C(C)C)c2c(c1)C(c3cc(OC(C)C)cc(OC(C)C)c3)=C[C]2[Ru-2]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1(OC(C)C)cc(OC(C)C)c2c(c1)C(c3cc(OC(C)C)cc(OC(C)C)c3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 NHC.081 Ru-4 in Bidange2014
621 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 82.0 91.0 74.6 30 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 Ru-5 in Bidange2014
622 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 91.0 96.0 87.4 35 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
623 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 91.0 97.0 88.3 35 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 Ru-7 in Bidange2014
624 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 83.0 97.0 80.5 32 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 Ru-8 in Bidange2014
625 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 84.0 96.0 80.6 32 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 Ru-9 in Bidange2014
626 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 40.0 0.0 0.0 0 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 25000.0 CC(=O)COc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)COc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.037 Ru-10 in Bidange2014
627 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 70.0 91.0 63.7 64 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 Ru-2 in Bidange2014
628 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 73.0 91.0 66.4 66 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 10000.0 c1(OC(C)C)cc(OC(C)C)c2c(c1)C(c3cc(OC(C)C)cc(OC(C)C)c3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1(OC(C)C)cc([O+]7C(C)C)c2c(c1)C(c3cc(OC(C)C)cc(OC(C)C)c3)=C[C]2[Ru-2]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1(OC(C)C)cc(OC(C)C)c2c(c1)C(c3cc(OC(C)C)cc(OC(C)C)c3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 NHC.081 Ru-4 in Bidange2014
629 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 82.0 96.0 78.7 79 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
630 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 43.0 98.0 42.1 42 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous pentane 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
631 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 36.0 89.0 32.0 32 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous cyclohexane 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
632 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 52.0 91.0 47.3 47 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous dibutyl ether 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
633 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 63.0 92.0 58.0 58 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous cyclopentyl methyl ether 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
634 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 71.0 95.0 67.5 67 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous dimethyl carbonate 10000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
635 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 83.0 93.0 77.2 77 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 10000.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 Ru-7 in Bidange2014
636 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 83.0 96.0 79.7 80 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 10000.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 Ru-9 in Bidange2014
637 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 79.0 92.0 72.7 145 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 5000.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
638 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 31.0 90.0 27.9 112 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 2500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 Ru-6 in Bidange2014
639 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 82.0 92.0 75.4 151 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 5000.0 CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccc(S(=O)(=O)N(C)C)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccc(S(=O)(=O)N(C)C)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.012 Ru-7 in Bidange2014
640 C=C (flow, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 79.0 93.0 73.5 147 O GC, IS: dodecane flow Schlenk tube argon 25 3.0 None None homogeneous toluene 5000.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 Ru-9 in Bidange2014
641 C=C (20 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 98.0 92.0 90.2 360 O GC, IS: dodecane batch reactor argon 120 16.0 None None homogeneous toluene 2500.0 CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)C(F)(F)F)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.016 Ru-11 in Bidange2014
642 C=C (20 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 86.0 92.0 79.1 632 O GC, IS: dodecane batch reactor argon 120 16.0 None None homogeneous toluene 1250.0 CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)C(F)(F)F)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.016 Ru-11 in Bidange2014
643 C=C (20 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 55.0 90.0 49.5 792 O GC, IS: dodecane batch reactor argon 120 16.0 None None homogeneous toluene 625.0 CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)C(F)(F)F)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.016 Ru-11 in Bidange2014
644 C=C (20 bar, 99.95%) CCCCCCCC/C=C\CCCCCCCC#N C18:1 (major, n.r.%) N#CCCCCCCCC=C CCCCCCCCC=C N#CCCCCCCCC=CCCCCCCCC#N CCCCCCCCC=CCCCCCCCC None 28.0 89.0 24.9 830 O GC, IS: dodecane batch reactor argon 120 16.0 None None homogeneous toluene 300.0 CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccc(NC(=O)C(F)(F)F)cc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccc(NC(=O)C(F)(F)F)cc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.016 Ru-11 in Bidange2014
645 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 50.0 97.0 48.0 4800 S2 GC batch reactor None 40 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.49 2a in Zhang2013 (DOI: 10.1039/c3cc45823g)
646 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 16.0 96.0 15.0 10000 S2 GC batch reactor None 40 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 15.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.49 2a in Zhang2013
647 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 60.0 96.0 58.0 5800 S2 GC batch reactor None 40 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) 0 1 CAAC.50 2b in Zhang2013
648 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 30.0 96.0 29.0 19300 S2 GC batch reactor None 40 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 15.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) 0 1 CAAC.50 2b in Zhang2013
649 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 53.0 80.0 42.0 8000 S2 GC batch reactor None 40 1.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C(C)C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C(C)C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C(C)C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.51 2c in Zhang2013
650 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 36.0 95.0 35.0 3500 S2 GC batch reactor None 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.18 1a in Zhang2013
651 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 96% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 0.0 0.0 0.0 0 S2 GC batch reactor None 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 15.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.18 1a in Zhang2013
652 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 27.0 97.0 26.0 26000 S2 GC batch reactor None 40 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C(C)C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) 0 1 CAAC.50 2b in Zhang2013
653 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 0.0 0.0 0.0 0 S2 GC, IS: tridecane batch reactor argon 40 1.0 None None homogeneous CH2Cl2 (minimal amount) 1000.0 CC(C)Oc1ccccc1C=[Ru]5(OC(=O)C(C)(C)C)=C2N(CCN2c3c(C)cc(C)cc3C5)c4c(C)cc(C)cc4C CC(C)[O+]9c1ccccc1[CH][Ru-2]59(OC(=O)C(C)(C)C)[C+]2N(CCN2c3c(C)cc(C)cc3C5)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]75(OC(=O)C(C)(C)C)[C+]2N(CCN2c3c(C)cc(C)cc3C5)c4c(C)cc(C)cc4C 0 1 NHC.088 3 in Miyazaki2013 (DOI: 10.1021/ja4010267)
654 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 0.0 0.0 0.0 0 S2 GC, IS: tridecane batch reactor argon 40 1.0 None None homogeneous CH2Cl2 (minimal amount) 100.0 CC(C)Oc1ccccc1C=[Ru]5(OC(=O)C(C)(C)C)=C2N(CCN2c3c(C)cc(C)cc3C5)c4c(C)cc(C)cc4C CC(C)[O+]9c1ccccc1[CH][Ru-2]59(OC(=O)C(C)(C)C)[C+]2N(CCN2c3c(C)cc(C)cc3C5)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]75(OC(=O)C(C)(C)C)[C+]2N(CCN2c3c(C)cc(C)cc3C5)c4c(C)cc(C)cc4C 0 1 NHC.088 3 in Miyazaki2013
655 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 84.2 95.0 80.0 800 S2 GC, IS: tridecane batch reactor argon 40 1.0 None None homogeneous CH2Cl2 (minimal amount) 1000.0 CC(C)Oc1ccccc1C=[Ru]7(O[N+](=O)[O-])=C2N(CCN2c3c(C)cc(C)cc3C)C45CC6CC(CC(C6)C4)C57 CC(C)[O+]9c1ccccc1[CH][Ru-2]79(O[N+](=O)[O-])[C+]2N(CCN2c3c(C)cc(C)cc3C)C45CC6CC(CC(C6)C4)C57 CC(C)Oc1ccccc1[CH]9C[CH2][Ru-]79(O[N+](=O)[O-])[C+]2N(CCN2c3c(C)cc(C)cc3C)C45CC6CC(CC(C6)C4)C57 0 1 NHC.089 5 in Miyazaki2013
656 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 12.6 95.0 12.0 1160 S2 GC, IS: tridecane batch reactor argon 40 1.0 None None homogeneous CH2Cl2 (minimal amount) 100.0 CC(C)Oc1ccccc1C=[Ru]7(O[N+](=O)[O-])=C2N(CCN2c3c(C)cc(C)cc3C)C45CC6CC(CC(C6)C4)C57 CC(C)[O+]9c1ccccc1[CH][Ru-2]79(O[N+](=O)[O-])[C+]2N(CCN2c3c(C)cc(C)cc3C)C45CC6CC(CC(C6)C4)C57 CC(C)Oc1ccccc1[CH]9C[CH2][Ru-]79(O[N+](=O)[O-])[C+]2N(CCN2c3c(C)cc(C)cc3C)C45CC6CC(CC(C6)C4)C57 0 1 NHC.089 5 in Miyazaki2013
657 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 26.0 61.5 16.0 16 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 [Ru]-1 in Behr2012 (DOI: 10.1039/c2ra22499b)
658 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 98.0 55.1 54.0 54 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 [Ru]-2 in Behr2012
659 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 26.0 73.1 19.0 19 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P(C4CCCCC4)(C5CCCCC5)C6CCCCC6.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 0 1 G1-ind.1 [Ru]-3 in Behr2012
660 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 98.0 64.3 63.0 63 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
661 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 98.0 33.7 33.0 33 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7.n8ccccc8 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-3](Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)([N+]7=CC=CC=C7)[N+]8=CC=CC=C8 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-2]7(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 0 2 NHC.082 [Ru]-5 in Behr2012
662 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 42.0 71.4 30.0 30 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P4(CC(C)C)C5CCCC4CCC5.P6(CC(C)C)C7CCCC6CCC7 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+]4(CC(C)C)C5CCCC4CCC5)[P+]6(CC(C)C)C7CCCC6CCC7 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+]4(CC(C)C)C5CCCC4CCC5 0 1 G1-ind.3 [Ru]-6 in Behr2012
663 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 99.0 36.4 36.0 36 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n7ccccc7 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[N+]7=CC=CC=C7 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.028 [Ru]-7 in Behr2012
664 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 84.0 61.9 52.0 52 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(C=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(C=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]17C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.083 [Ru]-8 in Behr2012
665 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 93.0 71.0 66.0 66 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 s1cccc1C=[Ru](Cl)(Cl)=C2N(C=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 s1cccc1[CH][Ru-2](Cl)(Cl)([C+]2N(C=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 s1cccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C=CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.084 [Ru]-9 in Behr2012
666 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 91.0 68.1 62.0 62 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 s1cccc1C=[Ru](Cl)(Cl)=C2N(C(C)=C(C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 s1cccc1[CH][Ru-2](Cl)(Cl)([C+]2N(C(C)=C(C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 s1cccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(C(C)=C(C)N2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.085 [Ru]-10 in Behr2012
667 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 89.0 40.4 36.0 36 O GC batch reactor None 50 8.0 None None homogeneous toluene 10000.0 CC(=O)C(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(=O)C(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.039 [Ru]-11 in Behr2012
668 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 91.0 76.9 70.0 1400 O GC batch reactor None 50 3.0 None None homogeneous toluene 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
669 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 92.0 76.1 70.0 700 O GC batch reactor None 50 3.0 None None homogeneous toluene 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
670 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 89.0 73.0 65.0 260 O GC batch reactor None 50 3.0 None None homogeneous toluene 2500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
671 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 88.0 73.9 65.0 130 O GC batch reactor None 50 3.0 None None homogeneous toluene 5000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
672 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 85.0 71.8 61.0 81 O GC batch reactor None 50 3.0 None None homogeneous toluene 7500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
673 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 87.0 72.4 63.0 63 O GC batch reactor None 50 3.0 None None homogeneous toluene 10000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
674 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 82.0 78.0 64.0 51 O GC batch reactor None 50 3.0 None None homogeneous toluene 12500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
675 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 87.0 71.3 62.0 41 O GC batch reactor None 50 3.0 None None homogeneous toluene 15000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
676 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 80.0 72.5 58.0 580 O GC batch reactor None 50 3.0 None None homogeneous cyclohexane 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
677 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 84.0 58.3 49.0 490 O GC batch reactor None 50 3.0 None None homogeneous hexadecane 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
678 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 84.0 60.7 51.0 510 O GC batch reactor None 50 3.0 None None homogeneous isopropanol 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
679 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 85.0 68.2 58.0 580 O GC batch reactor None 50 3.0 None None homogeneous methanol 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
680 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 86.0 81.4 70.0 700 O GC batch reactor None 50 3.0 None None homogeneous ethyl acetate 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
681 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 84.0 78.6 66.0 660 O GC batch reactor None 50 3.0 None None homogeneous tetrahydrofuran 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
682 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 96.0 95.8 92.0 1840 O GC batch reactor None 80 18.0 None None homogeneous toluene 500.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
683 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 97.0 95.9 93.0 930 O GC batch reactor None 80 18.0 None None homogeneous toluene 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
684 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 98.0 86.7 85.0 425 O GC batch reactor None 80 18.0 None None homogeneous toluene 2000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
685 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)OC C18:1 98% COC(=O)CCCCCCCC=C CCCCCCC(O)CC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCC(O)CC=CCC(O)CCCCCC None 99.0 83.8 83.0 830 O GC batch reactor None 80 3.0 None None homogeneous toluene 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
686 C=C (20 bar) CCCCCCC(O)C/C=C\CCCCCCCC(=O)O C18:1 80% OC(=O)CCCCCCCC=C CCCCCCC(O)CC=C None CCCCCCC(O)CC=CCC(O)CCCCCC None 97.0 76.3 74.0 740 O GC batch reactor None 80 3.0 None None homogeneous toluene 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
687 C=C (20 bar) Castor oil n.r.% C(COC(=O)CCCCCCCC=C)(COC(=O)CCCCCCCC=C)OC(=O)CCCCCCCC=C CCCCCCC(O)CC=C None None None 0.0 0.0 0.0 0 O GC batch reactor None 80 3.0 None None homogeneous toluene 1000.0 c6ccc1c(c6)C(c5ccccc5)=CC1=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C7CCCCC7)(C8CCCCC8)C9CCCCC9 c6ccc1c(c6)C(c5ccccc5)=C[C]1[Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C7CCCCC7)(C8CCCCC8)C9CCCCC9 - 0 1 NHC.076 [Ru]-4 in Behr2012
688 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 3.0 99.0 3.0 600 S2 GC, IS: toluene continuous-flow None 0 3.0 microreactor (MiChS system) None homogeneous toluene 150.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 6 in Park2011 (10.1021/ol200634y)
689 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 65.0 96.0 62.4 5800 S2 GC, IS: toluene continuous-flow None 30 2.0 microreactor (MiChS system) None homogeneous toluene 300.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 6 in Park2011
690 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 39.0 94.8 37.0 7500 S2 GC, IS: toluene continuous-flow None 30 2.0 microreactor (MiChS system) None homogeneous toluene 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 7 in Park2011
691 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 69.0 93.7 64.7 4400 S2 GC, IS: toluene continuous-flow None 30 2.0 microreactor (MiChS system) None homogeneous toluene 300.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 7 in Park2011
692 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 58.0 45.0 26.1 11000 S2 GC, IS: toluene continuous-flow None 40 1.0 microreactor (MiChS system) None homogeneous toluene 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 8 in Park2011
693 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.0 43.5 25.7 5400 S2 GC, IS: toluene continuous-flow None 30 2.0 microreactor (MiChS system) None homogeneous toluene 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 8 in Park2011
694 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 61.0 41.0 25.0 5300 S2 GC, IS: toluene continuous-flow None 40 1.0 microreactor (MiChS system) None homogeneous toluene 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 8 in Park2011
695 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 54.0 52.0 28.1 13500 S2 GC, IS: toluene continuous-flow None 40 1.0 microreactor (MiChS system) None homogeneous toluene 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.013 9 in Park2011
696 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 57.0 50.0 28.5 6800 S2 GC, IS: toluene continuous-flow None 40 1.0 microreactor (MiChS system) None homogeneous toluene 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.013 9 in Park2011
697 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 61.0 58.0 35.4 22300 S2 GC, IS: toluene continuous-flow None 40 0.7 microreactor (MiChS system) None homogeneous toluene 50.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C).P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C))[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C) 0 1 NHC.001 10 in Park2011
698 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 63.0 55.0 34.7 10900 S2 GC, IS: toluene continuous-flow None 40 0.7 microreactor (MiChS system) None homogeneous toluene 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C).P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C))[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C) 0 1 NHC.001 10 in Park2011
699 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 80.0 87.0 69.6 27200 S2 GC, IS: toluene continuous-flow None 40 1.0 microreactor (MiChS system) None homogeneous toluene 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 11 in Park2011
700 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 81.0 84.0 68.0 13300 S2 GC, IS: toluene continuous-flow None 40 1.0 microreactor (MiChS system) None homogeneous toluene 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 11 in Park2011
701 C=C (4 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 97% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 72.0 88.0 63.4 12400 S2 GC, IS: toluene continuous-flow None 40 0.5 microreactor (MiChS system) None homogeneous toluene 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 11 in Park2011
702 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 54.0 86.0 46.0 4620 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C(C)c4c5ccccc5ccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(C)c4c5ccccc5ccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(C)c4c5ccccc5ccc4 0 1 NHC.066 12 in Thomas2011 (DOI: 10.1021/ja200246e)
703 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 11.0 77.0 9.0 845 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)C(C)c4c5ccccc5ccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)C(C)c4c5ccccc5ccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)C(C)c4c5ccccc5ccc4 0 1 NHC.067 13 in Thomas2011
704 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 70.0 58.0 41.0 817 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)(C)C)cccc3)C(C)c4c5ccccc5ccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)(C)C)cccc3)C(C)c4c5ccccc5ccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)(C)C)cccc3)C(C)c4c5ccccc5ccc4 0 1 NHC.068 14 in Thomas2011
705 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 52.0 86.0 45.0 4450 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C(C)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(C)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(C)c4ccccc4 0 1 NHC.069 15 in Thomas2011
706 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 42.0 86.0 36.0 3600 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 0 1 NHC.070 16 in Thomas2011
707 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 83.0 86.0 72.0 1440 S2 GC batch reactor argon 40 2.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 0 1 NHC.070 16 in Thomas2011
708 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 12.0 87.0 10.0 2010 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 0 1 NHC.070 16 in Thomas2011
709 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 81.0 41.0 4090 S2 GC batch reactor argon 50 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 0 1 NHC.070 16 in Thomas2011
710 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 47.0 79.0 37.0 3680 S2 GC batch reactor argon 60 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C(CC)c4ccccc4 0 1 NHC.070 16 in Thomas2011
711 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.0 87.0 51.0 5070 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 0 1 NHC.071 17 in Thomas2011
712 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 89.0 88.0 78.0 1570 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 0 1 NHC.071 17 in Thomas2011
713 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 12.0 86.0 10.0 2050 S2 GC batch reactor argon 40 2.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 0 1 NHC.071 17 in Thomas2011
714 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 67.0 81.0 55.0 5460 S2 GC batch reactor argon 50 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 0 1 NHC.071 17 in Thomas2011
715 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 68.0 81.0 55.0 5470 S2 GC batch reactor argon 60 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4c5ccccc5CCC4 0 1 NHC.071 17 in Thomas2011
716 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 52.0 89.0 46.0 4604 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4C(C)C5CC(C4)C5(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4C(C)C5CC(C4)C5(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4C(C)C5CC(C4)C5(C)(C) 0 1 NHC.072 18 in Thomas2011
717 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 86.0 88.0 76.0 1520 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4C(C)C5CC(C4)C5(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4C(C)C5CC(C4)C5(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4C(C)C5CC(C4)C5(C)(C) 0 1 NHC.072 18 in Thomas2011
718 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 15.0 95.0 15.0 1460 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) 0 1 NHC.073 19 in Thomas2011
719 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 48.0 95.0 46.0 913 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 500.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) 0 1 NHC.073 19 in Thomas2011
720 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 5.0 96.0 5.0 1010 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)C4CC5CCC4(C)C5(C)(C) 0 1 NHC.073 19 in Thomas2011
721 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 17.0 69.0 11.0 1120 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)C4c5ccccc5CCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)C4c5ccccc5CCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)C4c5ccccc5CCC4 0 1 NHC.074 20 in Thomas2011
722 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 40.0 79.0 31.0 3080 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)CCCC.P(C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)CCCC)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)CCCC 0 1 NHC.075 21 in Thomas2011
723 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 65.0 82.0 53.0 1060 S2 GC batch reactor argon 40 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 500.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)CCCC.P(C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)CCCC)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)CCCC 0 1 NHC.075 21 in Thomas2011
724 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 19.0 79.0 14.0 2880 S2 GC batch reactor argon 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 50.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)CCCC.P(C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)CCCC)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)CCCC 0 1 NHC.075 21 in Thomas2011
725 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 4.0 80.0 3.0 1680 S2 GC batch reactor argon 40 2.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 20.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)CCCC.P(C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)CCCC)[P+](C4CCCCC4)(C5CCCCC5)C6CCCCC6 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)CCCC 0 1 NHC.075 21 in Thomas2011
726 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 58.0 93.0 54.0 5400 S2 GC batch reactor None 40 2.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 6 in Schrodi2008 (DOI: 10.1002/clen.200800088)
727 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 54.0 89.0 48.0 4800 S2 GC batch reactor None 60 0.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 6 in Schrodi2008
728 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 94.0 48.0 4800 S2 GC batch reactor None 40 0.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 HG1 7 in Schrodi2008
729 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 64.0 44.0 28.0 2800 S2 GC batch reactor None 40 2.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 8 in Schrodi2008
730 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 64.0 44.0 28.0 2800 S2 GC batch reactor None 60 0.25 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 8 in Schrodi2008
731 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 60.0 33.0 20.0 2000 S2 GC batch reactor None 40 0.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 9 in Schrodi2008
732 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 68.0 47.0 32.0 3200 S2 GC batch reactor None 60 0.25 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 HG2 9 in Schrodi2008
733 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 69.0 55.0 38.0 3800 S2 GC batch reactor None 40 1.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C))[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C) 0 1 NHC.001 10 in Schrodi2008
734 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 61.0 36.0 22.0 22000 S2 GC batch reactor None 40 1.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 10.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C))[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3(C(C)C))c4c(C(C)C)cccc4(C(C)C) 0 1 NHC.001 10 in Schrodi2008
735 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 70.0 56.0 39.0 3900 S2 GC batch reactor None 40 0.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.013 11 in Schrodi2008
736 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 79.0 71.0 56.0 5600 S2 GC batch reactor None 60 0.25 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.013 11 in Schrodi2008
737 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 69.0 57.0 39.0 11000 S2 GC batch reactor None 40 0.25 None None homogeneous neat (catalyst added in CH2Cl2 solution) 35.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.013 11 in Schrodi2008
738 C=C (55 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 87.0 80.0 70.0 7000 S2 GC batch reactor None 25 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.013 11 in Schrodi2008
739 C=C (55 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 63.0 32.0 12800 S2 GC batch reactor None 25 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 25.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.013 11 in Schrodi2008
740 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 62.0 34.0 21.0 2100 S2 GC batch reactor None 40 0.25 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C.n5ccccc5.n6ccccc6 c1ccccc1[CH][Ru-3](Cl)(Cl)([C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C)([N+]5=CC=CC=C5)[N+]6=CC=CC=C6 None 0 1 NHC.002 12 in Schrodi2008
741 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 50.0 7.0 3.0 329 S2 GC batch reactor None 40 0.25 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.n5ccccc5.n6ccccc6 c1ccccc1[CH][Ru-3](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)([N+]5=CC=CC=C5)[N+]6=CC=CC=C6 None 0 1 NHC.003 13 in Schrodi2008
742 C=C (12 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 66.0 53.0 35.0 3560 S2 GC batch reactor None 40 21.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 N(C)(C)c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C [N+]7(C)(C)c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C N(C)(C)c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.018 14 in Schrodi2008
743 C=C (12 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 79.0 72.0 57.0 5710 S2 GC batch reactor None 60 6.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 N(C)(C)c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C [N+]7(C)(C)c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C N(C)(C)c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.018 14 in Schrodi2008
744 C=C (12 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 81.0 67.0 54.0 5410 S2 GC batch reactor None 80 2.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 N(C)(C)c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C [N+]7(C)(C)c1ccccc1[CH][Ru-2]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C N(C)(C)c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.018 14 in Schrodi2008
745 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 58.0 55.0 32.0 3200 S2 GC batch reactor None 40 23.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 N(C)(C)c1ccccc1C=[Ru](Br)(Br)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C [N+]7(C)(C)c1ccccc1[CH][Ru-2]7(Br)(Br)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C N(C)(C)c1ccccc1[CH]7C[CH2][Ru-]7(Br)(Br)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.019 15 in Schrodi2008
746 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 78.0 73.0 57.0 5640 S2 GC batch reactor None 60 3.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 N(C)(C)c1ccccc1C=[Ru](Br)(Br)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C [N+]7(C)(C)c1ccccc1[CH][Ru-2]7(Br)(Br)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C N(C)(C)c1ccccc1[CH]7C[CH2][Ru-]7(Br)(Br)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.019 15 in Schrodi2008
747 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 51.0 69.0 35.0 3570 S2 GC batch reactor None 40 6.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 N(C)(C)c1ccccc1C=[Ru](I)(I)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C [N+]7(C)(C)c1ccccc1[CH][Ru-2]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C N(C)(C)c1ccccc1[CH]7C[CH2][Ru-]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.020 16 in Schrodi2008
748 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 59.0 90.0 53.0 5370 S2 GC batch reactor None 60 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 N(C)(C)c1ccccc1C=[Ru](I)(I)=C2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C [N+]7(C)(C)c1ccccc1[CH][Ru-2]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C N(C)(C)c1ccccc1[CH]7C[CH2][Ru-]7(I)(I)[C+]2N(CCN2c3c(C(C)C)cccc3C(C)C)c4c(C(C)C)cccc4C(C)C 0 1 NHC.020 16 in Schrodi2008
749 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 35.0 86.0 30.0 2990 S2 GC batch reactor None 60 0.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](OC(=O)C(F)(F)F)(OC(=O)C(F)(F)F)=C2N(CC(C)(C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)[O+]7c1ccccc1[CH][Ru-2]7(OC(=O)C(F)(F)F)(OC(=O)C(F)(F)F)[C+]2N(CC(C)(C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C CC(C)Oc1ccccc1[CH]7C[CH2][Ru-]7(OC(=O)C(F)(F)F)(OC(=O)C(F)(F)F)[C+]2N(CC(C)(C)CN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 NHC.004 17 in Schrodi2008
750 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 77.0 66.0 51.0 5200 S2 GC batch reactor None 60 4.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 [B-](F)(F)(F)F.C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)[CH][Ru-](Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.033 18 in Schrodi2008
751 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 76.0 61.0 46.0 4680 S2 GC batch reactor None 80 0.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 [B-](F)(F)(F)F.C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)[CH][Ru-](Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.033 18 in Schrodi2008
752 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 71.0 59.0 42.0 4200 S2 GC batch reactor None 40 20.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 [B-](F)(F)(F)F.C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)[CH][Ru-](Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C C1CCCCC1[P+](C5CCCCC5)(C6CCCCC6)[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 1 1 NHC.033 18 in Schrodi2008
753 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 61.0 92.0 56.0 5600 S2 GC batch reactor None 40 22.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) 0 1 CAAC.13 19 in Schrodi2008
754 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 61.0 93.0 57.0 10000 S2 GC batch reactor None 40 20.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 50.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) 0 1 CAAC.13 19 in Schrodi2008
755 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 46.0 94.0 43.0 4200 S2 GC batch reactor None 40 6.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C4(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)CCCCC4 0 1 CAAC.18 20 in Schrodi2008
756 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 73.0 73.0 53.0 5300 S2 GC batch reactor None 40 0.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 21 in Schrodi2008
757 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 75.0 75.0 56.0 16000 S2 GC batch reactor None 40 1.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 35.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 21 in Schrodi2008
758 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 42.0 83.0 35.0 35000 S2 GC batch reactor None 40 0.5 None None homogeneous neat (catalyst added in CH2Cl2 solution) 10.0 CC(C)Oc1ccccc1C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)[O+]7c1ccccc1[CH][Ru-]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) CC(C)Oc1ccccc1[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(CC)cccc3CC)(C)(C) 0 1 CAAC.10 21 in Schrodi2008
759 C=C (10 bar, 99.9%) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 60.0 90.0 54.0 5440 S2 GC batch reactor None 40 22.0 None None homogeneous neat (catalyst added in CH2Cl2 solution) 100.0 [B-](F)(F)(F)F.C1CCCCC1[P+](C4CCCCC4)(C5CCCCC5)C=[Ru](Cl)(Cl)=C2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) C1CCCCC1[P+](C4CCCCC4)(C5CCCCC5)[CH][Ru](Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) C1CCCCC1[P+](C4CCCCC4)(C5CCCCC5)[CH]7C[CH2][Ru]7(Cl)(Cl)[C]2C(CC(C)(C)N2c3c(C(C)C)cccc3C(C)C)(C)(C) 1 1 CAAC.52 22 in Schrodi2008
760 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 53.0 98.9 52.4 2621 U GC, IS: tetradecane batch autoclave argon 50 2.0 None None homogeneous neat (catalyst added in toluene solution) 200.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 1 in Forman2006 (doi: 10.1016/j.jorganchem.2006.06.021)
761 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 60.0 99.2 59.5 3229 U GC, IS: tetradecane batch autoclave argon 50 2.0 None None homogeneous neat (catalyst added in toluene solution) 200.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P4(C6CCCCC6)C5CCCC4CCC5.P7(C9CCCCC9)C8CCCC7CCC8 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+]4(C6CCCCC6)C5CCCC4CCC5)[P+]7(C9CCCCC9)C8CCCC7CCC8 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+]4(C6CCCCC6)C5CCCC4CCC5 0 1 G1-ind.2 2 in Forman2006
762 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 49.6 99.0 49.1 4918 U GC, IS: tetradecane batch autoclave argon 50 2.0 None None homogeneous neat (catalyst added in toluene solution) 100.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 1 in Forman2006
763 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 69.8 99.1 69.2 6917 U GC, IS: tetradecane batch autoclave argon 50 2.0 None None homogeneous neat (catalyst added in toluene solution) 100.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P4(C6CCCCC6)C5CCCC4CCC5.P7(C9CCCCC9)C8CCCC7CCC8 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+]4(C6CCCCC6)C5CCCC4CCC5)[P+]7(C9CCCCC9)C8CCCC7CCC8 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+]4(C6CCCCC6)C5CCCC4CCC5 0 1 G1-ind.2 2 in Forman2006
764 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 43.0 98.5 42.4 8542 U GC, IS: tetradecane batch autoclave argon 50 2.0 None None homogeneous neat (catalyst added in toluene solution) 50.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 1 in Forman2006
765 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 63.9 97.4 62.2 12450 U GC, IS: tetradecane batch autoclave argon 50 2.0 None None homogeneous neat (catalyst added in toluene solution) 50.0 c1ccc2c(c1)C(c3ccccc3)=CC2=[Ru](Cl)(Cl).P4(C6CCCCC6)C5CCCC4CCC5.P7(C9CCCCC9)C8CCCC7CCC8 c1ccc2c(c1)C(c3ccccc3)=C[C]2[Ru-2](Cl)(Cl)([P+]4(C6CCCCC6)C5CCCC4CCC5)[P+]7(C9CCCCC9)C8CCCC7CCC8 c1ccc2c(c1)C(c3ccccc3)=C[C]27C[CH2][Ru-]7(Cl)(Cl)[P+]4(C6CCCCC6)C5CCCC4CCC5 0 1 G1-ind.2 2 in Forman2006
766 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 14.0 91.0 12.7 4247 U GC, IS: tetradecane batch autoclave argon 60 2.0 None None homogeneous neat (catalyst added in toluene solution) 30.0 c1ccccc1C=[Ru](Cl)(Cl).P(C2CCCCC2)(C3CCCCC3)C4CCCCC4.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+](C2CCCCC2)(C3CCCCC3)C4CCCCC4 0 1 G1 1 in Forman2004 (DOI: 10.1021/om049370c)
767 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 37.0 58.0 21.5 7153 U GC, IS: tetradecane batch autoclave argon 60 2.0 None None homogeneous neat (catalyst added in toluene solution) 30.0 c1ccccc1C=[Ru](Cl)(Cl)=C2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C.P(C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH][Ru-2](Cl)(Cl)([C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C)[P+](C5CCCCC5)(C6CCCCC6)C7CCCCC7 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[C+]2N(CCN2c3c(C)cc(C)cc3C)c4c(C)cc(C)cc4C 0 1 G2 2 in Forman2004
768 C=C (10 bar) CCCCCCCC/C=C\CCCCCCCC(=O)OC C18:1 99% COC(=O)CCCCCCCC=C CCCCCCCCC=C COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC CCCCCCCCC=CCCCCCCCC None 43.0 98.0 42.1 14047 U GC, IS: tetradecane batch autoclave argon 60 2.0 None None homogeneous neat (catalyst added in toluene solution) 30.0 c1ccccc1C=[Ru](Cl)(Cl).P2(C4CCCCC4)C3CCCC2CCC3.P5(C7CCCCC7)C6CCCC5CCC6 c1ccccc1[CH][Ru-2](Cl)(Cl)([P+]2(C4CCCCC4)C3CCCC2CCC3)[P+]5(C7CCCCC7)C6CCCC5CCC6 c1ccccc1[CH]7C[CH2][Ru-]7(Cl)(Cl)[P+]2(C4CCCCC4)C3CCCC2CCC3 0 1 G1-phob 6 in Forman2004

Note: First deployed November 2025. Updates (if any) will be listed here.