CONJUGATED NITROALKENES IN CYCLOADDITION REACTIONS. 17. MECHANISM OF (2+3) CYCLOADDITION BETWEEN (<i>E</i>)-3,3,3-TRIFLUORO-1-NITROPROP-1-ENE AND (<i>Z</i>)-<i>C</i>-PHENYL-<i>N</i>-METHYLNITRONE IN THE LIGHT OF REACTIVITY INDICES THEORY AND B3LYP/6-31G*

Authors

  • R. Jasiński Institute of Organic Chemistry and Technology, Cracow University of Technology
  • J. Socha Institute of Organic Chemistry and Technology, Cracow University of Technology
  • A. Barański Institute of Organic Chemistry and Technology, Cracow University of Technology

DOI:

https://doi.org/10.1007/791

Keywords:

nitroalkene, nitrones, B3LYP/6-31G* calculations, (2 3) cycloaddition

Abstract

Analysis of the reactivity indices shows the polar character of the (2+3) cycloaddition between (E)-3,3,3-trifluoro-1-nitroprop-1-ene and (Z)-C-phenyl-N-methylnitrone. This is confirmed by exploration of reaction paths by B3LYP/6-31G(d) algorithm. Although the transition complexes involved in the reaction mechanism are considerably asymmetric and polar, the reactions proceed via a one-step mechanism.

Also published in Chemistry of Heterocyclic Compounds, 2013, 49 (7), pp 1055-1060

http://link.springer.com/article/10.1007/s10593-013-1343-9

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Published

2013-07-02

Issue

No. 7 (2013)

Section

Original Papers