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Reactions of dichlorocarbene with N-(2,2-diphenylvinylidene)-anilines. 1,3-Dipolar derivatives of ketenimine-ylides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Ketenimine-ylides Ph2C=C-N+(=CCl2)Ar, formed by the reaction of N-(2,2-diphenylvinylidene)anilines with dichlorocarbene, generated by heating sodium trichloroacetate in chloroform, undergoes [2+3]-cycloaddition with dimethylacetylenedicarboxylate, methyl methacrylate, and dimethyl fumarate to give pyrrole derivatives; in addition, pyridine derivatives are formed in the reaction with dimethyl fumarate. In the absence of a dipolar compound, ketenimines-ylides give N-aryl-N-(2,2-diphenylvinyl)amides of di- and trichloracetic acids.

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Literature Cited

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Authors and Affiliations

  1. A. A. Zhdanov Leningrad State University, 199004, Leningrad

    A. F. Khlebnikov, M. S. Novikov & R. R. Kostikov

Authors
  1. A. F. Khlebnikov
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  2. M. S. Novikov
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  3. R. R. Kostikov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1336–1342, October, 1987.

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Khlebnikov, A.F., Novikov, M.S. & Kostikov, R.R. Reactions of dichlorocarbene with N-(2,2-diphenylvinylidene)-anilines. 1,3-Dipolar derivatives of ketenimine-ylides. Chem Heterocycl Compd 23, 1070–1076 (1987). https://doi.org/10.1007/BF00476534

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  • DOI: https://doi.org/10.1007/BF00476534

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