Diphenylacetylene → HCID 19601750, compound

HRID 610719Notes

Reaction equation

HRID 610719 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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=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

5

Reactant 2

HCID 10390Diphenylacetylene2×HCID 102356231HCID 102356231, compound2×

Product 1

HCID 19601750HCID 19601750, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 241BenzeneSolvent2×

Procedure

Hydrosilation of diphenylacetylene with bis(dichlorosilyl)trichlorosilylmethane in the presence of Pd(PPh3)4. Into the same apparatus as described in Example 1 were add 0.98 g of bis(dichlorosilyl)trichlorosilylmethane, 0.101 g of Pd(PPh3)4, and 25 ml of dried benzene to form a mixture. The mixture was brought to reflux temperature and 0.52 g of diphenylacetylene in 10 ml of benzene were added over a 30 minute period. The mixture was stirred at reflux temperature for an additional 18 hours and then the solvent removed at atmospheric pressure. The residue was vacuum distilled to yield a mixture comprising 0.417 g of 1,1,3,3-tetrachloro-2-trichlorosilyl-4,5-diphenyl-1,3-disilacyclopentane (TCD-GC area 25%).

Workup

  1. customto form a mixture
  2. additionwere added over a 30 minute period
  3. temperatureat reflux temperature for an additional 18 hours
  4. customthe solvent removed at atmospheric pressure
  5. distillationdistilled

Sources & evidence

ORD record
ord-6c47efcc63f2450cb363cc528d8e7fd3
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

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