Phenylacetylene → Dichloro[(dichlorosilyl)methyl](2-phenylethenyl)silane

HRID 610731Notes

Reaction equation

HRID 610731 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][SiH:10]([CH2:12][SiH:13]([Cl:15])[Cl:14])[Cl:11]>C1C=CC=CC=1>[Cl:9][Si:10]([Cl:11])([CH2:12][SiH:13]([Cl:15])[Cl:14])[CH:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 10821Phenylacetylene2×HCID 57370748Bisdichlorosilylmethane2×

Product 1

HCID 71376014Dichloro[(dichlorosilyl)methyl](2-phenylethenyl)silaneYield 5.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Hydrosilation of phenylacetylene with bis(dichlorosilyl)methane in the presence of RhCl(PPh3)3. Into the same apparatus as described in Example 1 were added 0.99 g of bis(dichlorosilyl)methane, 0.102 g of RhCl(PPh3)3, and 20 ml of dried benzene. The flask content was heated to reflux and 0.52 ml of phenylacetylene was added over a 10 minute period. The flask content was refluxed, with stirring, for another 2 hours and then the solvent removed at atmospheric pressure. The products were vacuum distilled at 67 Pa to give a mixture comprising 0.9 g of 3,3,5,5-tetrachloro-1-phenyl-3,5-disilapent-1-ene (TCD-GC area 5.5%) and 3,3,5,5-tetrachloro-1,7-diphenyl-3,5-disilahepta-1,6-diene (TCD-GC area 66.5%).

Workup

  1. temperatureThe flask content was heated
  2. temperatureto reflux
  3. temperatureThe flask content was refluxed
  4. customthe solvent removed at atmospheric pressure
  5. distillationdistilled at 67 Pa

Sources & evidence

ORD record
ord-668d04143ead4829be91172cd89e4c7f
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

Loading…