Russian Journal of Organic Chemistry

, Volume 43, Issue 2, pp 286–296 | Cite as

Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines

  • A. S. Konev
  • M. S. Novikov
  • A. F. Khlebnikov
Article

Abstract

N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-π-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dimethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-π-cyclization, in the presence of acid catalysts suffer isomerization into α-fluoroimines and 1,3-disubstituted indoles.

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Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • A. S. Konev
    • 1
  • M. S. Novikov
    • 1
  • A. F. Khlebnikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

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