Diphenylacetylene → HCID 19601750, compound

HRID 610713Notes

Reaction equation

HRID 610713 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]([CH:18]([SiH:23]([Cl:25])[Cl:24])[Si:19]([Cl:22])([Cl:21])[Cl:20])[Cl:17]>C1C=CC=CC=1>[Cl:17][Si:16]1([Cl:15])[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:23]([Cl:24])([Cl:25])[CH:18]1[Si:19]([Cl:22])([Cl:20])[Cl:21]

Participants

4

Reactant 2

HCID 10390Diphenylacetylene2×HCID 102356231HCID 102356231, compound2×

Product 1

HCID 19601750HCID 19601750, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Hydrosilation of diphenylacetylene with bis(dichlorosilyl)trichlorosilylmethane in the presence of H2PtCl6 /IPA. Into the same apparatus as described in Example 1 were placed 0.60 g of diphenylacetylene, 1.06 g of bis(dichlorosilyl)trichlorosilylmethane, 31 μl of 0.1 M H2PtCl6/IPA, and 25 ml of dried benzene forming a mixture. The resulting mixture, with stirring, was refluxed for 5 hours and then the solvent removed at atmospheric pressure. The residue was vacuum distilled at 67 Pa to yield a mixture comprising 1.42 g of 1,1,3,3-tetrachloro-2-trichlorosilyl-4,5-diphenyl-1,3-disilacyclopentane (TCD-GC area 71.2%) and 3,3,5,5-tetrachloro-4-trichlorosilyl-1,2,6,7-tetraphenyl-3,5-disilahepta-1,6-diene (TCD-GC area 5.9%). 1,1,3,3-Tetrachloro-2-trichlorosilyl-4,5-diphenyl- 1,3-disilacyclopentane=1H-NMR (CDCl3, ppm): 1.82 (s, 1H, SiCHSi), 3.35-3.44 (m, 2H, CHPh), 7.06-7.18 (m, 5H, ArH).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customthe solvent removed at atmospheric pressure
  3. distillationdistilled at 67 Pa

Sources & evidence

ORD record
ord-dac2513f2bcd428bb6e9a1347d9b1ace
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

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