An analysis of the regioselectivity of 1,3-Dipolar cycloaddition reactions of benzonitrile N-Oxides based on global and local electrophilicity and nucleophilicity indices

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Abstract

The regioselectivity of the 1,3-dipolar cycloaddition (13DC) reactions of benzonitrile N-oxides (BNOs) with electrophilic and nucleophilic alkenes has been analyzed by using global and local nucleophilicity and electrophilicity reactivity indices defined within the conceptual DFT. The BNOs react with, electron-deficient and electron-rich ethylenes, but the regioselectivities of these polar reactions are different. Whereas the reactions with electron-rich ethylenes are completely regioselective, yielding 5-isoxazolines, a change in the regioselectivity is observed in the reactions with electron-deficient ethylenes, which yield a mixture of 4- and 5isoxazolines. Analysis of the energies, geometries, and electronic structures of the transition-state structures involved in the 13DC reactions between the BNOs and two electronically activated ethylenes are in complete agreement with, the analysis of the global and local electrophilicity and nucleophilicity reactivity indices.

Original languageEnglish
Pages (from-to)3036-3044
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number18
DOIs
Publication statusPublished - Jun 2009

Keywords

  • Cycloaddition
  • Electrophilicity
  • Heterocyeles
  • Nitrile n-oxides
  • Nucleophilicity
  • Regioselectivity

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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