Silicon in Synthesis. 8. Vinyltrimethylsilane, a Convenient Ethylene Equivalent for the Synthesis of Vinyl Aryl Sulfides, Vinyl Aryl Sulfoxides, Thiosilylketene Acetals, and Fused Cyclopentenones

Article abstract of DOI:10.1021/jo01294a026

Vinyltrimethylsilane reacts with a variety of arylsulfenyl chlorides to give 2-chloro-1-(trimethylsilyl)ethyl aryl sulfide adducts 9-13.These adducts can be converted into vinyl aryl sulfides and vinyl aryl sulfoxides, and for the case of 2-chloro-1-(trimethylsilyl)ethyl phenyl sulfide (11), treatment with 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) gave 1-(trimethylsilyl)-1-(phenylthio)ethylene (24). α,β-Unsaturated acid chlorides react with vinyltrimethylsilane in the presence of stannic tetrachloride to give fused cyclopentenones.In all of the reaction described, vinyltrimethylsilane serves as a convenient ethylene equivalent.