Bulletin of the Chemical Society of Japan p. 1205 - 1208 (1982)
Update date:2022-08-02
Topics:
Agawa, Toshio
Ishikawa, Minori
Komatsu, Mitsuo
Ohshiro, Yoshiki
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.
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