The unusual reactivity of benzene and monosubstituted benzenes towards tetracyanoethylene oxide: A theoretical study
- Jiménez-Osés, G. 1
- Elguero, J. 2
- García, J.I. 1
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1
Instituto de Nanociencia y Materiales de Aragón
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2
Instituto de Química Médica
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ISSN: 1144-0546
Argitalpen urtea: 2009
Alea: 33
Zenbakia: 3
Orrialdeak: 471-478
Mota: Artikulua
Beste argitalpen batzuk: New Journal of Chemistry
Laburpena
The cycloaddition of tetracyanoethylene oxide (TCNEO) with benzene and benzene derivatives, and the subsequent evolution of the corresponding cycloadducts is theoretically investigated using DFT and highly correlated ab initio calculations. Both the relative reactivity of the different aromatic compounds, as well as the regioselectivity of the cycloaddition is explained in light of the theoretical study. Insights in the formation of arylmalononitriles, which gives potential synthetic applications to this process, are also offered. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2009.