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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 8, Issue 2, 2011

Page: [108 - 118] Pages: 11

DOI: 10.2174/157017811794697412

Price: $65


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).

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

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