Acetylene → 1,1,3,3-Tetrachloro-1,3-disilacyclopent-4-ene

HRID 610727Notes

Reaction equation

HRID 610727 reaction equation
[CH:1]#[CH:2].[Cl:3][SiH:4]([CH2:6][SiH:7]([Cl:9])[Cl:8])[Cl:5]>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:3][Si:4]1([Cl:5])[CH:2]=[CH:1][Si:7]([Cl:9])([Cl:8])[CH2:6]1

Participants

5

Reactant 2

HCID 6326Acetylene2×HCID 57370748Bisdichlorosilylmethane2×

Product 1

HCID 121214481,1,3,3-Tetrachloro-1,3-disilacyclopent-4-eneYield 55.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 241BenzeneSolvent

Procedure

Hydrosilation of acetylene with bis(dichlorosilyl)methane in the presence of Pd(PPh3)4. Into the same apparatus as described in Example 1 were placed 10 g of bis(dichlorosilyl)methane, 0.103 g of Pd(PPh3)4, and 20 ml of dried benzene. Acetylene gas was blown into the flask at 90 ml/min for 3 hours. The products were vacuum distilled at 67 Pa to yield a mixture comprising 8.29 g of 1,1,3,3-tetrachloro-1,3-disilacyclopent-4-ene (TCD-GC area 55.2%); 3,3,5,5-tetrachloro-3,5-disilapent-1-ene (TCD-GC area 12.7%); 1,1,3,3-tetrachloro-1,3-disilacyclopentane (TCD-GC area 5.3%); and 1,1,3,3,6,6,8,8-octachloro-1,3,6,8-tetrasilaoctane (TCD-GC area 0.3%).

Workup

  1. distillationdistilled at 67 Pa

Sources & evidence

ORD record
ord-b17f2b41cb554f0b8718168438d2cd79
Source dataset
uspto-grants-1999_12
Patent number
US05998649

Reaction notes

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