Diphenylacetylene → HCID 123340255, compound

HRID 610721Notes

Reaction equation

HRID 610721 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:22]([Cl:24])[Cl:23])[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])[CH:18]1[SiH:22]([Cl:24])[Cl:23]

Participants

4

Reactant 2

HCID 10390Diphenylacetylene2×HCID 71354001Methanetriyltris(dichlorosilane)2×

Product 1

HCID 123340255HCID 123340255, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Hydrosilation of diphenylacetylene with tris(dichlorosilyl)methane in the presence of H2PtCl6 /IPA. Into the same apparatus as described in Example 1 were place 3.39 g of diphenylacetylene, 5.91 g of tris(dichlorosilyl)methane, 40 ml of dried benzene, and 100 μl of a 0.1 M H2PtCl6 /IPA solution to form a mixture. The mixture was stirred for 5 hours at reflux temperature and then the solvent removed at atmospheric pressure. The residue was vacuum distilled at 67 Pa to yield a mixture comprising 7.51 g of 1,1,3,3-tetrachloro-2-dichlorosilyl-4,5-diphenyl-1,3-disilacyclopentane (TCD-GC area of 12.3%) and 1,1,3,3 -tetrachloro-2-(1,2-dichloro-2,3-diphenyl- 1 -sila-2-propenyl)-4,5-diphenyl-1,3-disilacyclopentane (TCD-GC area 74%). 1,1,3,3-Tetrachloro-2-dichlorosilyl4,5-diphenyl-1,3-disilacyclopentane=1H-NMR (CDCl3, ppm): 1.72 (d, 3.4 Hz, 1H, SiCHSi), 3.47-3.53 (m, 2H, CHPh), 5.8 (d, 3.5 Hz, 1H, SiH), 7.15-7.28 (m, 10 H, ArH). 1,1,3,3-Tetrachloro-2-(1,2-dichloro-2,3-diphenyl-1 -sila-2-propenyl)-4,5-diphenyl-1,3-disilacyclopentane=1H-NMR (CDC13, ppm): 1.73(s, 1H, SiCHSi), 3.52-3.55 (m, 2H, CHPh), 7.12-7.50 (m, 21H, C=CHPh and ArH).

Workup

  1. temperatureat reflux temperature
  2. customthe solvent removed at atmospheric pressure
  3. distillationdistilled at 67 Pa

Sources & evidence

ORD record
ord-2db888deee7145d6a5b4251f44580a0b
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

Loading…