1,3-Butadiene → 1,1-Dichloro-1-silacyclo-3-pentene

HRID 1583088Notes

Reaction equation

HRID 1583088 reaction equation
C=CC=C.Cl[SiH](Cl)Cl.[Cl:9][Si:10]([Cl:20])([Cl:19])[CH2:11][CH:12]=[CH:13][CH2:14][Si](Cl)(Cl)Cl>[Cl-].C([P+](CCCC)(CCCC)CCCC)CCC>[CH2:14]1[Si:10]([Cl:20])([Cl:19])[CH2:11][CH:12]=[CH:13]1.[CH2:11]([Si:10]([Cl:20])([Cl:19])[Cl:9])[CH:12]=[CH:13][CH3:14]

Participants

6

Reactant 3

HCID 78451,3-ButadieneHCID 24811TrichlorosilaneHCID 53686027HCID 53686027, compound

Product 2

HCID 1366721,1-Dichloro-1-silacyclo-3-penteneYield 68%HCID 543214CROTYLTRICHLOROSILANEYield 20%

Reagents, catalysts & solvents 1

HCID 75311Tetrabutylphosphonium chlorideCatalyst

Conditions

Temperature
150 °C

Procedure

In a a 25 ml oven dried stainless steel tube ,1,3-butadiene (1.27 g, 23.26 mmol), trichlorosilane (14.7 g, 108.53 mmol) and tetrabutylphosphonium chloride (0.68 g, 2.31 mmol) were added under a dry nitrogen atmosphere. After sealing the cylinder with a cap, the reactor was maintained at 150° C. for 2 hours. The resulting mixture was distilled to yield 2.44 g (yield: 68%) of 1,1-dichlorosilacyclo-3-pentene main product, 0.88 g (yield: 20%) of crotyltrichlorosilane by product, and 0.37 g (yield: 5%) of trace 1,4-bis(trichlorosilyl)-2-butene.

Workup

  1. distillationThe resulting mixture was distilled

Sources & evidence

ORD record
ord-0ee3451c15c242fcb1570e666a6e7e96
Source dataset
uspto-grants-2004_05
Patent number
US06740766B2

Reaction notes

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