Phenylacetylene → HCID 19601754, compound

HRID 610718Notes

Reaction equation

HRID 610718 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][SiH:10]([CH:12]([SiH:17]([Cl:19])[Cl:18])[Si:13]([Cl:16])([Cl:15])[Cl:14])[Cl:11]>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.C1C=CC=CC=1>[Cl:11][Si:10]1([Cl:9])[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[Si:17]([Cl:18])([Cl:19])[CH:12]1[Si:13]([Cl:16])([Cl:14])[Cl:15]

Participants

5

Reactant 2

HCID 10821Phenylacetylene2×HCID 102356231HCID 102356231, compound2×

Product 1

HCID 19601754HCID 19601754, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 241BenzeneSolvent

Procedure

Hydrosilation of phenylacetylene with bis(dichlorosilyl)trichlorosilylmethane in the presence of Pd(PPh3)4. Into the same apparatus as described in Example 1 were added 1.0 g of bis(dichlorosilyl)trichlorosilylmethane, 0.102 g of Pd(PPh3)4, and 25 ml of dried benzene to form a mixture. The mixture was brought to reflux temperature and 0.32 ml of phenylacetylene added over a 10 minute period. The mixture was stirred at reflux temperature for an additional 8 hours and then the solvent removed at atmospheric pressure. The residue was vacuum distilled at 67 Pa to yield a mixture comprising 0.348 g of 1,1,3,3-tetrachloro-2-trichlorosilyl-4-phenyl-1,3-disilacyclopent-4-ene (TCD-GC area 43.9%).

Workup

  1. customto form a mixture
  2. additionadded over a 10 minute period
  3. temperatureat reflux temperature for an additional 8 hours
  4. customthe solvent removed at atmospheric pressure
  5. distillationdistilled at 67 Pa

Sources & evidence

ORD record
ord-1340f3861ad140ebbd84ebccbdda447a
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

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