Reaction of 1-lithio-1-arylthio(or alkylthio)methyltrimethylsilane with acid derivatives. A novel synthesis of functionalized vinyl sulfides.
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概要
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Reactions of 1-lithio-1-phenylthiomethyl- (<B>1a</B>) and 1-lithio-1-methylthiomethyltrimethylsilane (<B>1b</B>) with amides, an ester, acid anhydrides, a urea, and a carbonate are described which provide useful routes to functionalized vinyl sulfides. The reaction of <B>1</B> with amides gave β-functionalized vinyl sulfides, 1-dialkylamino-2-phenylthio (or methylthio)ethylenes, in 40–95% yields and the reaction could be extended to the sulfonyl derivatives of <B>1</B> 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 <B>1a</B> followed by addition of benzaldehyde.
- 公益社団法人 日本化学会の論文
著者
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Komatsu Mitsuo
Department Of Applied Chemistry Faculty Of Engineering Osaka University
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Ohshiro Yoshiki
Department Of Applied Chemistry Faculty Of Engineering Osaka University
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Agawa Toshio
Department of Petroleum Chemistry, Faculty of Engineering, Osaka University
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Ishikawa Minori
Department of Petroleum Chemistry, Faculty of Engineering, Osaka University
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Agawa Toshio
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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