Regio-and stereospecific cleavage of #alpha#,#beta#-epoxysilanes with lithium phenylsulfide

摘要

Trimethyl- or dimethylphenylsilylepoxides react with lithium phenylsulfide to give regio- and stereodefined vinyl sulfides resulting from #alpha#-ring opening and Peterson elimination. When the epoxide the bulky tert-butyldiphenylsilyl group the reaction is more puzzling.Depending on the #beta#-substitution and the presence of aluminium chloride,we obtained silyl enol ethers, #alpha#-silylaldehydes or #alpha#-hydroxy-#beta#-phenylthiosilanes, all resulting from #beta#-opening.