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

HRID 610729Notes

Reaction equation

HRID 610729 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>O1CCCC1>[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

5

Reactant 3

HCID 241BenzeneHCID 10821Phenylacetylene2×HCID 57370748Bisdichlorosilylmethane2×

Product 1

HCID 71376014Dichloro[(dichlorosilyl)methyl](2-phenylethenyl)silaneYield 27.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrosilation of phenylacetylene with bis(dichlorosilyl)methane in the presence of H2PtCl6 /THF. Into the same apparatus as described in Example 1 were added 1 g of bis(dichlorosilyl)methane, 20 μl of 0.1 M H2PtCl6 in THF (tetrahydrofuran) solution, and 20 ml of dried benzene. The flask content was heated to reflux and 0.52 ml of phenylacetylene was added over a ten minute period. The flask content was refluxed, with stirring, for another 8 hours and then the solvent removed at atmospheric pressure. The products were vacuum distilled at 67 Pa to give a mixture comprising 1.66 g of 3,3,5,5-tetrachloro-1-phenyl-3,5-disilapenta-1-ene (TCD-GC area 27.3%) and 3,3,5,5-tetrachloro-1,7-diphenyl-3,5-disilahepta-1,6-diene (TCD-GC area 26.4%).

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-4de2b1b3a328468aaa621dca56360a30
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

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