Chemistry of Heterocyclic Compounds

, Volume 40, Issue 2, pp 203–210 | Cite as

Synthesis and Properties of Azoles and Their Derivatives. 54. The Regioselectivity of [2+3] Cycloaddition Of C,C,N-Triphenyl- and Z-C,N-Diphenylnitrones With β- and α-Substituted Nitroethylenes in Light of Frontier Molecular Orbital Theory

  • R. Jasinski
  • A. Ciezkowska
  • A. Lyubimtsev
  • A. Baranski


Using quantum-chemical calculations we have carried out an analysis of frontier molecular orbital interactions in the [2+3] cycloaddition reactions of C,C,N-triphenyl- and Z-C,N-diphenylnitrones with β- and α-substituted nitroethylenes. In all of the examples studied the orbital effects lead to the formation of the corresponding 4-nitroisoxazolidines.

nitroalkenes nitrones regioselectivity [2+3] cycloaddition frontier molecular orbitals 


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Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

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

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