The Cycloaddition Reaction of Isonitrile to Ketenimine Formed by the Reaction of Isonitrile with Carbene

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概要

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• The reaction of several 2-, 4-, and/or 6-fnethyl-substituted phenylisonitrile with dihalocarbene and diphenylcarbene has been studied. The reaction of methyl-substituted phenylisonitrile with dihalocarbene gave indolenine or indoloquinoline derivatives <I>via</I> ketenimine intermediate which might be produced by α-addition of carbene to isonitrile. In contrast, the reaction of 2,6-dimethylphenylisonitrile with diphenylcarbene presumably formed by photolysis of diphenyldiazomethane gave <I>N</I>-(2,6-dimethylphenyl)diphenylketenimine, and further caused a cycloaddition reaction with isonitrile to yield indonimine derivatives. The structure of these products are discussed on the basis of the spectral data and chemical reactions. The mechanistic pathway of these reactions and the effect of methyl substituent in the cyclization stage are also discussed.

• 公益社団法人 日本化学会の論文

著者

• Mizuno Haruo

  Faculty of Pharmaceutical Sciences, University of Tokyo

• Takizawa Takeo

  Faculty of Pharmaceutical Sciences, University of Tokyo

• Takizawa Takeo

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• Obata Naruyoshi

  Faculty of Pharmaceutical Sciences, University of Tokyo

• Koitabashi Takeo

  Faculty of Pharmaceutical Sciences, University of Tokyo

• Obata Naruyoshi

  Faculty of Pharmaceutical Sciences, The University of Tokyo

関連論文

• The Cycloaddition Reaction of Isonitrile to Ketenimine Formed by the Reaction of Isonitrile with Carbene
• Catalytic Activities of a Polyoxime–cobalt Complex for the Addition Reaction of an Alcohol to Acrylaldehyde and for the Polymerization of Styrene
• Photochemical reaction of diphenylcyclobutenedione derivatives. Formation and reaction of conjugated bisketene and its N-analog.
• 1,3-Dithian-2-one tosylhydrazone. Synthesis and carbenoid decomposition.

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