Understanding the diels-alder reactivity of superelectrophilic nitrobenzofuroxans and related 10π-heteroaromatics through DFT-based electrophilicity

Sami Lakhdar, Guillaume Berionni, Régis Goumont, Francois Terrier

Research output: Contribution to journalArticlepeer-review

Abstract

A close relationship between the superelectrophilic reactivity of a large set of nitrobenzofuroxans and related 10π-heteroaromatics (nitrobenzofurazans, nitrobenzotriazoles, nitrotetrazolopyridines..) and the high propensity of these compounds to contribute to a variety of Diels-Alder processes has been experimentally established. This relationship suggests that most of the corresponding cycloadditions must be strongly polar processes. In this paper, it is shown that this important mechanistic outcome is fully supported by an analysis of the reactions on the basis of the reactivity descriptors defined by Parr within the DFT theory, namely the global electrophilicity parameter ω (and the related δNmax parameter) and the local electrophilicity parameter (ωk).

Original languageEnglish
Pages (from-to)108-118
Number of pages11
JournalLetters in Organic Chemistry
Volume8
Issue number2
DOIs
Publication statusPublished - Feb 2011
Externally publishedYes

Keywords

  • DFT electrophilicity descriptors
  • Electrophilicity scales
  • Polar Diels-Alder cycloadditions
  • Superelectrophilic heteroaromatics

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