Studies of Acenaphthene Derivatives. XX. The Reactions of Benzylideneacenaphthenones with Sulfonium Ylides
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概要
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The reactions of benzylideneacenaphthenones with sulfonium ylides were studied extensively. Although the reactions of benzylidene- and <I>p</I>-methylbenzylideneacenaphthenone with dimethylsulfonium methylide gave only resinous materials, the <I>p</I>-chlorobenzylidene derivative condensed with the ylide to afford the corresponding spiroxirane compound in a good yield. In the reactions with dimethyloxosulfonium methylide and carbonyl-stabilized sulfonium ylides such as ethyl (dimethylsulfuranilidene) acetate and dimethylsulfonium phenacylide, benzylidene-acenaphthenones gave the corresponding spirocyclopropyl ketones in good yields. The products obtained in the latter reactions were established to be <I>cis</I>-cyclopropyl compounds on the basis of NMR spectral studies. On the other hand, ethoxycarbonylmethyleneacenaphthenone condensed with carbonyl-stabilized sulfonium ylides to give <I>trans</I>-cyclopropyl ketones. On the basis of these results, the reaction mechanism was discussed. Also, bis-2,2′-methyleneacenaphthenone reacted with ethyl (dimethylsulfuranilidene) acetate to give the bis-spirocyclopropyl ketone.
- 公益社団法人 日本化学会の論文
著者
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Tsuge Otohiko
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University
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Tsuge Otohiko
Research Institute of Industrial Science, Kyushu University Hakozaki
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Shinkai Ichiro
Research Institute of Industrial Science, Kyushu University Hakozaki
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