Reaction of 1-Lithio-1-arylthio(or alkylthio)methyltrimethylsilane with Acid Derivatives. A Novel Synthesis of Functionalized Vinyl Sulfides

Article abstract of DOI:10.1246/bcsj.55.1205

Reactions of 1-lithio-1-phenylthiomethyl- (1a) and 1-lithio-1-methylthiomethyltrimethylsilane (1b) with amides, an ester, acid anhydrides, a urea, and a carbonate are described which provide useful routes to functionalized vinyl sulfides.The reaction of 1 with amides gave β-functionalized vinyl sulfides, 1-dialkylamino-2-phenylthio (or methylthio)ethylenes, in 40-95percent yields and the reaction could be extended to the sulfonyl derivatives of 1 to afford 1-dialkylamino-2-phenylsulfonyl(or methylsulfonyl)ethylenes.Although ethyl benzoate and some acid anhydrides were not good substrates for this reaction, tetramethylurea and diethyl carbonate gave α-functionalized vinyl sulfides, 1-amidovinyl- and 1-(ethoxycarbonyl)vinyl sulfides, in moderate yields when treated with 1a followed by addition of benzaldehyde.