CONJUGATED NITROALKENES IN CYCLOADDITION REACTIONS. 18. REGIO- AND STEREOSELECTIVITY OF (2+3) CYCLOADDITION REACTIONS BETWEEN <i>gem</i>-CHLORONITROETHENE AND (<i>Z</i>)-<i>C,N</i>-DIARYLNITRONES

Authors

  • R. Jasiński Institute of Organic Chemistry and Technology, Cracow University of Technology
  • M. Mikulska Institute of Organic Chemistry and Technology, Cracow University of Technology
  • O. Koifman Ivanovo State University of Chemistry and Technology
  • A. Barański Institute of Organic Chemistry and Technology, Cracow University of Technology

DOI:

https://doi.org/10.1007/431

Keywords:

nitroalkene, nitrone, (2 3) cycloaddition, regioselectivity, stereoselectivity

Abstract

(2+3) Сycloadditions of gem-chloronitroethene to diarylnitrones proceed regiospecifically and lead to stereoisomeric mixtures of 3,4-cis- and 3,4-trans-2,3-diaryl-4-chloro-4-nitroisoxazolidines. The interpretation of the regiospecificity of the reaction based on the theory of reactivity indices shows that its course is determined by an attack of the nucleophilic center at the nitrone oxygen atom to the electrophilic center at the gem-chloronitroethene.

Also published in Chemistry of Heterocyclic Compounds, 2013, 49 (8), pp 1188-1194

http://link.springer.com/article/10.1007/s10593-013-1362-6

 

Author Biographies

R. Jasiński, Institute of Organic Chemistry and Technology, Cracow University of Technology

Radomir Jasiński

M. Mikulska, Institute of Organic Chemistry and Technology, Cracow University of Technology

Maria Mikulska

O. Koifman, Ivanovo State University of Chemistry and Technology

Oskar Koifman

A. Barański, Institute of Organic Chemistry and Technology, Cracow University of Technology

Andrzej Barański

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Published

2013-06-17

Issue

No. 8 (2013)

Section

Original Papers