Alkoxymethylthiomethylsilanes as a Synthetic Equivalent of Thiocarbonyl Ylides. Synthesis of 1,3-Oxathiolanes and Tetrahydrothiophenes

Abstract

Abstract Alkoxymethylthiomethylsilanes, easily prepared, react nucleophilically with aldehydes by the action of fluoride ion and electrophilically with silyl enol ethers in the presence of a Lewis acid. These products can be converted to 1,3-oxathiolanes by acid catalysis and tetrahydrothiophenes by fluoride ion-promoted intramolecular alkylthiomethylation, respectively. By both sequential reactions alkoxymethylthiomethylsilanes serve as substituted thiocarbonyl ylide synthons.