Russian Journal of Organic Chemistry

, Volume 40, Issue 10, pp 1493–1499 | Cite as

1,3-dipolar cycloaddition of fluorinated azomethine ylides at the C=N bond

  • M. S. Novikov
  • A. F. Khlebnikov
  • M. A. Egarmin
  • J. Kopf
  • R. R. Kostikov
Article

Abstract

Azomethine ylides generated by reaction of difluorocarbene with N-alkyl- and N-arylimines derived from benzaldehyde and benzophenone react with N-benzylidenebenzenesulfonamide in a regioselective fashion, yielding the corresponding imidazolidin-4-ones via 1,3-dipolar cycloaddition at the C=N bond. Ylides generated from benzaldehyde imines give rise to mixtures of stereoisomeric 2,5-diphenyl-1-(phenylsulfonyl)-imidazolidin-4-ones, the cis isomer prevailing.

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Copyright information

© MAIK “Nauka/Interperiodica” 2004

Authors and Affiliations

  • M. S. Novikov
    • 1
  • A. F. Khlebnikov
    • 1
  • M. A. Egarmin
    • 1
  • J. Kopf
    • 2
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institut für anorganische ChemieHamburgGermany

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