Stereochemistry of elimination reactions of halohydrin derivatives and related compounds with butyllithium.
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概要
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The <I>erythro</I> and <I>threo</I> isomers of 1-bromo-2-methoxy-1,2-diphenylethane (<B>1</B>), 1-bromo-2-acetoxy-1,2-diphenylethane (<B>2</B>), 1-bromo-2-methylsulfonyloxy-1,2-diphenylethane (<B>3</B>), 1-bromo-2-methylthio-1,2-diphenylethane (<B>4</B>), stilbene dibromide (<B>6</B>), and stilbene dichloride have been prepared. These compounds were allowed to react with butyllithium in various solvents to give <I>cis</I>- and <I>trans</I>-stilbenes. Depending on the solvent, the stereochemistry of the elimination of <B>1</B> changed from a complete <I>syn</I>-type (in nonpolar solvents) to a less-selective type. The same tendency was observed in the cases of <B>2</B> and <B>3</B>. In contrast, <I>anti</I>-elimination was favored for <B>4</B> and <B>6</B>, and a different type of solvent effect was observed. Elimination reactions with lithium metal and pentylmagnesium bromide were also carried out. Possible mechanisms for eliminations are discussed.
- 公益社団法人 日本化学会の論文
著者
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Kasai Yasuhiro
Department Of Applied Physics Faculty Of Engineering Osaka University
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Sugita Toshio
Department Of Electrical Engineering Science University Of Tokyo
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Nakagawa Junichi
Department Of Food Science And Technology Faculty Of Bioindustry Tokyo University Of Agriculture
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Ichikawa Katsuhiko
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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Kasai Yasuhiro
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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Nishimoto Kazuhito
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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