Studies on organosilicon chemistry. 115. Alkoxymethylthiomethylsilanes as a Synthetic Equivalent of Thiocarbonyl Ylides. Synthesis of 1, 3-Oxathiolanes and …
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 ...