Understanding the Diels-Alder Reactivity of Superelectrophilic Nitrobenzofuroxans and Related 10π-Heteroaromatics through DFT-Based Electrophilicity Descriptors

Title: Understanding the Diels-Alder Reactivity of Superelectrophilic Nitrobenzofuroxans and Related 10π-Heteroaromatics through DFT-Based Electrophilicity Descriptors

Volume: 8 Issue: 2

Author(s): Sami Lakhdar, Guillaume Berionni, Regis Goumont and Francois Terrier

Affiliation:

Keywords: Polar Diels-Alder cycloadditions, superelectrophilic, heteroaromatics, DFT electrophilicity descriptors, electrophilicity scales, 4, 6-dinitrobenzofuroxan (DNBF), oxadiazole, electrophiles, cyclohexadiene, heterocycles

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).

Cite this article as:

Lakhdar Sami, Berionni Guillaume, Goumont Regis and Terrier Francois, Understanding the Diels-Alder Reactivity of Superelectrophilic Nitrobenzofuroxans and Related 10π-Heteroaromatics through DFT-Based Electrophilicity Descriptors, Letters in Organic Chemistry 2011; 8 (2) . https://dx.doi.org/10.2174/157017811794697412