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Chemistry of Heterocyclic Compounds

, Volume 40, Issue 2, pp 203–205 | Cite as

Synthesis and Properties of Azoles and Their Derivatives. 52. Periselectivity of [2+3] Cycloaddition of Nitrones to trans-β-Cyanonitroethylene in the Light of FMO Theory

  • R. Jasinski
  • A. Ciezkowska
  • A. Baranski
Article

Abstract

[2+3] Cycloaddition reaction of nitrones with trans-β-cyanonitroethylene may theoretically lead to regioisomeric nitroisoxazolidines and isomeric oxadiazoles. However, 4- and 5-nitroisoxazolidines were really obtained as only reaction products. Periselectivity of this reaction is rationalized in terms of the FMO theory.

periselectivity FMO nitrone nitroalkene AM1 calculations 

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Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • R. Jasinski
    • 1
  • A. Ciezkowska
    • 1
  • A. Baranski
    • 1
  1. 1.Institute of Organic Chemistry and TechnologyCracow University of TechnologyCracowPoland

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