Stereochemical studies of the electrolytic reactions of organic compounds. V. The electro-reductive cyclization of 1-acyl-8-benzoylnaphthalenes to 1,2-acenaphthenediols.
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概要
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The electrolytic reductions of several 1-acyl-8-benzoylnaphthalenes were carried out by means of controlled potential electrolysis at a mercury cathode in various catholytes. The isomeric ratio of the <I>cis</I>- and <I>trans</I>-1,2-acenaphthenediols thus formed depended on the kind of acyl group, supporting electrolyte, organic solvent in the catholyte, and cathode potential applied. The mechanism of the reductive cyclization is discussed from the stereochemical point of view, and it is proposed that the cyclization may occur not only by the intramolecular coupling of the biradical intermediate, but also by the intramolecular nucleophilic addition of the anionic part of the carbanion intermediate to its unreacted carbonyl group.
- 公益社団法人 日本化学会の論文
著者
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NONAKA Tsutomu
Department of Electronic Chemistry, Tokyo Institute of Technology
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Nonaka Tsutomu
Department Of Electric Chemistry Tokyo Institute Of Technology
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Asai Mitsuo
Department of Electronic Chemistry, Tokyo Institute of Technology
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