SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. 54. THE REGIOSELECTIVITY OF [2+3] CYCLOADDITION OF C,C,N-TRIPHENYL- AND <i>Z</i>-C,N-DIPHENYLNITRONES WITH β- AND α- SUBSTITUTED NITROETHYLENES IN LIGHT OF FRONTIER MOLECULAR ORBITAL THEORY

Authors

  • Р. Ясиньски Institute of Organic Chemistry and Technology Cracow University of Technology 31-155 Cracow
  • А. Ценжковска Institute of Organic Chemistry and Technology Cracow University of Technology 31-155 Cracow
  • А. Любимцев Institute of Organic Chemistry and Technology Cracow University of Technology 31-155 Cracow
  • А. Бараньски Institute of Organic Chemistry and Technology Cracow University of Technology 31-155 Cracow

Keywords:

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

Abstract

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.

How to Cite
Yasinski, R.; Tsenzhkovska, A.; Lyubimtsev, A.; Baranski, A. Chem. Heterocycl. Compd. 2004, 40, 206. [Khim. Geterotsikl. Soedin. 2004, 243.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000027893.83553.c2

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Published

2004-02-25

Issue

No. 2 (2004)

Section

Original Papers