SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. 52. PERISELECTIVITY OF [2+3] CYCLOADDITION OF NITRONES TO <i>trans</i>-β-CYANONITROETHYLENE IN THE LIGHT OF FMO THEORY

Authors

  • R. Jasiński Institute of Organic Chemistry and Technology, Cracow University of Technology, 31-155 Cracow
  • A. Ciężkowska Institute of Organic Chemistry and Technology, Cracow University of Technology, 31-155 Cracow
  • A. Barański Institute of Organic Chemistry and Technology, Cracow University of Technology, 31-155 Cracow

Keywords:

periselectivity, FMO, nitrone, nitroalkene, AM1 calculations

Abstract

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

How to Cite
Jasiński, R.; Ciężkowska, A.; Barański, A. Chem. Heterocycl. Compd. 2004, 40, 203. [Khim. Geterotsikl. Soedin. 2004, 239.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000027892.68786.a5

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Published

2004-02-25

Issue

No. 2 (2004)

Section

Original Papers