Journal of the Chemical Society, Dalton Transactions p. 2177 - 2181 (1975)
Update date:2022-08-29
Topics:
Haszeldine, Robert N.
Pool, Colin R.
Tipping, Anthony E.
Treatment of 1-chloro-2-fluoroethyl- or 1,2-dichloroethyl-trichlorosilane with quinoline gives trichloro(1-chlorovinyl)silane; trichloro(1,2-dibromoethyl)silane dehydrohalogenates similarly. In contrast 2-chloro-1-fluoro-ethyl- and 1,2-difluoroethyl-trichlorosilane give vinyl fluoride under comparable conditions. Both 1-chlorovinyl-and 1-bromovinyl-trifluorosilane, prepared from the trichlorosilyl analogues, decompose slowly at 280°C to afford acetylene and tetrahalogenosilanes via the suspected intermediacy of the alkylidenecarbene CH2:C:. Pyrolysis of (2-chloro-1-fluoroethyl)trifluorosilane gives vinyl chloride via a carbene intermediate, but the trichlorosilyl analogue yields the rearrangement compound dichloro(1,2-dichloroethyl)fluorosilane. 1,2-Difluoroethyl-trifluorosilane and -trichlorosilane both decompose via a non-carbene mechanism involving β elimination.
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