Solvolytic ring-opening reactions of gem-dichloroaziridines in the presence of sulfuric acid.
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概要
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Solvolytic ring-opening reactions of <I>gem</I>-dichloroaziridines in the presence of sulfuric acid were investigated. The reaction products from 1-aryl-2,2-dichloro-3-phenylaziridines varied with the kind of substituent at 3-position of the aziridine ring. 2,2-Dichloro-1,3-diphenylaziridine gave α-chloro-α-phenylacetanilide, 2,2-dichloro-3-methyl-3-phenyl-1-(<I>m</I>-tolyl)aziridine gave <I>N</I>-(<I>m</I>-tolyl)atropamide and 2,2-dichloro-1,3,3-triphenylaziridine gave 3,3-diphenyloxindole. 1-Benzyl-2,2-dichloro-3,3-diphenylaziridine and 2,2-dichloro-1 -phenethyl-3,3-diphenylaziridine gave 4,4-diphenyl-1,2,3,4-tetrahydroisoquinoline-3-one and 1,1-diphenyl-1,2,3,4,5-pentahydro-3-benzazepine-2-one, respectively. It was found that the substituent on C<SUP>3</SUP>-carbon determines the mode of reaction.
- 公益社団法人 日本化学会の論文
著者
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SENO Manabu
Institute of Industrial Science, The University of Tokyo
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Shiraishi Shinsaku
Institute Of Industrial Science The University Of Tokyo
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Suzuki Yukio
Institute For Agricultural And Biological Sciences Okayama University
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Asahara Teruzo
Institute of Industrial Science, The University of Tokyo
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Suzuki Yukio
Institute of Industrial Science, University of Tokyo
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