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

HRID 610728Notes

Reaction equation

HRID 610728 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]>>[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.[Cl:9][Si:10]([Cl:11])([CH2:12][Si:13]([Cl:15])([Cl:14])[CH:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 10821PhenylacetyleneHCID 57370748Bisdichlorosilylmethane

Product 2

HCID 54429571HCID 54429571, compoundYield 28.1%HCID 71376014Dichloro[(dichlorosilyl)methyl](2-phenylethenyl)silaneYield 61.3%

Procedure

Hydrosilation of phenylacetylene with bis(dichlorosilyl)methane in the presence of H2PtCl6. Into the same apparatus as described in Example 1 were placed 25 μl of 0.1 M H2PtCl6 /IPA under nitrogen and the isopropyl alcohol was removed. Then 4.95 g of bis(dichlorosilyl)methane, 20 ml of dried benzene, and 2.5 ml of phenylacetylene were added to the flask and the flask content refluxed for 2 hours. The solvent was removed from the flask at atmospheric pressure and the products distilled at 67 Pa to yield a mixture comprising 3,3,5,5-tetrachloro-1 -phenyl-3,5-disilapent-1 -ene (TCD-GC area 61.3%) and 3,3,5,5-tetrachloro-1,7-diphenyl-3,5-disilahepta-1,6-diene (TCD-GC area 28.1%). 3,3,5,5-Tetrachloro-1-phenyl-3,5-disilapent-1-ene=1H-NMR (CDCl3, ppm): 1.45 (s, 2H, SiCH2Si), 5.71 (s, 1H, SiH), 6.45 (d, J=18.8Hz, 2H, SiCH=CHPh), 7.26-7.53 (m, 7H, CHArH); 3,3,5,5-tetrachloro-1,7-diphenyl-3,5-disilahepta-1,6-diene=1H-NMR (CDCl3, ppm): 1.43 (s, 2H, SiCH2Si), 6.18 (s, 2H, SiCH=CHPh), 7.27-7.47 (m, 7H, CHArH).

Workup

  1. customthe isopropyl alcohol was removed
  2. additionThen 4.95 g of bis(dichlorosilyl)methane, 20 ml of dried benzene, and 2.5 ml of phenylacetylene were added to the flask
  3. temperaturethe flask content refluxed for 2 hours
  4. customThe solvent was removed from the flask at atmospheric pressure
  5. distillationthe products distilled at 67 Pa

Sources & evidence

ORD record
ord-74ba00bb58024b14901ed7dc022c4b4a
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

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