Phenylacetylene → 1,3-Disilacyclopent-4-ene, 1,1,3,3-tetrachloro-4-phenyl-

HRID 610732Notes

Reaction equation

HRID 610732 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]>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:9][Si:10]1([Cl:11])[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[Si:13]([Cl:15])([Cl:14])[CH2:12]1

Participants

5

Reactant 2

HCID 10821Phenylacetylene2×HCID 57370748Bisdichlorosilylmethane2×

Product 1

HCID 121214491,3-Disilacyclopent-4-ene, 1,1,3,3-tetrachloro-4-phenyl-Yield 48.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 241BenzeneSolvent

Procedure

Hydrosilation of phenylacetylene with bis(dichlorosilyl)methane in the presence of Pd(PPh3)4. Into the same apparatus as described in Example 1 were added 1 g of bis(dichlorosilyl)methane, 0.101 g of Pd(PPh3)4, and 20 ml of dried benzene. The flask content was heated to reflux and 0.52 ml of phenylacetylene was added over a ten minute period. The flask content was refluxed, with stirring, for another hours and then the solvent removed at atmospheric pressure. The products were vacuum distilled at 67 Pa to give a mixture comprising 0.89 g of 1,1,3,3-tetrachloro-4-phenyl-1,3-disilacyclopent-4-ene (TCD-GC area 48.2%) and 3,3,5,5-tetrachloro-1,7-diphenyl-3,5-disilahepta-1,6-diene (TCD-GC area6%).

Workup

  1. temperatureThe flask content was heated
  2. temperatureto reflux
  3. temperatureThe flask content was refluxed
  4. customthe solvent removed at atmospheric pressure
  5. distillationdistilled at 67 Pa

Sources & evidence

ORD record
ord-6434ff18243b4d17b167d364b033792b
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

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