Synthesis and chemical behaviour of thioacylsilanes (silyl thioketones). Part 1. Oxidation to S-oxides, conversion into silylated thiiranes, silylated triarylethylenes, and α-silylated sulphides

Abstract

Trimethylsilyl and triphenylsilylaryl thioketones have been synthesized by acid catalysed reaction of the corresponding ketones with hydrogen sulphide. Such silylated thioketones have been oxidized to give S-oxides and converted with diaryldiazomethanes into triaryl thiiranes; upon treatment with organolithium nucleophiles they undergo thiophilic addition. The ready desulphurization with triphenylphosphine of silylated thiirans to the corresponding silyl triaryl ethylenes is also reported.