Polyfluoroalkyl compounds of silicon. Part VIII. Reactions of silanes with vinyl fluoride and with 1-chloro-2-fluoroethylene

Abstract

Photochemical reactions of trichlorosilane, methyldichlorosilane, or trimethylsilane with vinyl fluoride gave the corresponding 2-fluororoethylsilanes (90–95% yields), hydrolysis or pyrolysis of which occurred viaβ-elimination of fluorine. The photochemical reaction of trichlorosilane with 1-chloro-2-fluoroethylene gave both 1:1 adducts. These were reduced by further reaction with silanes (SiHCl₃, MeSiHCl₂, or Me₃SiH) to give the isomeric fluoroethyltrichlorosilanes; abstraction of β-chlorine occurred 3·5 times as readily as abstraction of α-chlorine. Hydrolysis of CH₂F·CHCl·SiCl₃ and CH₂Cl·CHF·SiCl₃ occurred viaβ-elimination of halogen to give vinyl chloride and vinyl fluoride, respectively. Trimethylsilane reacted with 1-chloro-2-fluoroethylene to give chlorotrimethylsilane, 2-chloro-1-fluoroethyltrimethylsilane, and 1-fluoroethyltrimethylsilane. The recovered olefin contained vinyl fluoride.