Medium effects on stereochemistry of acid-catalyzed ethanolysis of trans-2,3-diphenyloxirane.
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概要
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The acid catalyzed ethanolysis of <I>trans</I>-2,3-diphenyloxirane was examined in a wide variety of binary ethanolic solvent systems. The reaction proceeded with 26% retention and 74% inversion of configuration in pure ethanol at 50 °C. The dilution of ethanol by hexane or benzene produced almost no change in stereochemistry of the ethanolysis. The addition of acetonitrile, nitromethane, or sulfolane to the ethanolic solution resulted in increased degrees of retention. In binary ethanolic mixtures containing DMSO, DMF, or HMPA, increased ratios of inverted product were obtained. The steric course of the ethanolysis could be controlled from 85% retention–15% inversion (CH<SUB>3</SUB>NO<SUB>2</SUB>:ethanol=20:2 by volume) to 10% retention–90% inversion (HMPA: ethanol=10:12) by the choice of co-solvent. The results are discussed in terms of the solvation-shell concept.
- 公益社団法人 日本化学会の論文
著者
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Inoue Masashi
Department Of Applied Physics Fukui University
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Sugita Toshio
Department Of Electrical Engineering Science University Of Tokyo
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Ichikawa Katsuhiko
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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Taguchi Yoshio
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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Taguchi Yoshio
Department of Hydrocarbon Chemistry, Faculty of Engineering Kyoto University
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