Diphenylacetylene → HCID 19601744, compound

HRID 610733Notes

Reaction equation

HRID 610733 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:15][SiH:16]([CH2:18][SiH:19]([Cl:21])[Cl:20])[Cl:17]>C1C=CC=CC=1>[Cl:15][Si:16]1([Cl:17])[CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[Si:19]([Cl:21])([Cl:20])[CH2:18]1.[Cl:15][Si:16]([Cl:17])([CH2:18][Si:19]([Cl:21])([Cl:20])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 10390Diphenylacetylene2×HCID 57370748Bisdichlorosilylmethane

Product 2

HCID 19601744HCID 19601744, compoundYield 71%HCID 54346223HCID 54346223, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Hydrosilation of diphenylacetylene in the presence Into the same apparatus as described in Example 1 were added 6.1 g of bis(dichlorosilyl)methane, 6.1 g of diphenylacetylene, 28.3 μI of 0.1 M H2PtCl6 /IPA, and 20 ml of dried benzene. The flask content was refluxed, with stirring, for 12 hours and then the solvent removed at atmospheric pressure. The products were vacuum distilled at 67 Pa to give a crude product mixture. Crystallization from benzene gave 7.83 g of 1,1,3,3-tetrachloro-4,5-diphenyl-1,3-disilacyclopentane (yield 71 %) and 0.7 g of 3,3,5,5-tetrachloro-1,2,6,7-tetraphenyl-3,5-disilahepta-1,6-diene (yield 4%). 1,1,3,3-Tetrachloro-4,5-diphenyl-1,3-disilacyclopentane=1H-NMR (CDCl3, ppm): 1.51 (s, 2H, SiCH2Si), 3.50 (s, 2H, CHCH), 7.12-7.28 (m, 1OH, ArH) and 3,3,5,5-tetrachloro-1,2,6,7-tetraphenyl-3,5-disilahepta-1,6-diene=1H-NMR (CDCl3, ppm): 1.28 (s, 2H, SiCH2Si), 7.07 (s, 1H, CHPh), 7.16-7.41 (m, 20H, ArH).

Workup

  1. temperatureThe flask content was refluxed
  2. customthe solvent removed at atmospheric pressure
  3. distillationdistilled at 67 Pa
  4. customto give a crude product mixture
  5. customCrystallization from benzene

Sources & evidence

ORD record
ord-0638c51a737f423eaa976d8ace84abb0
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

Loading…