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Issue 3, 2009
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The unusual reactivity of benzene and monosubstituted benzenes towards tetracyanoethylene oxide: a theoretical study

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Abstract

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.

Graphical abstract: The unusual reactivity of benzene and monosubstituted benzenes towards tetracyanoethylene oxide: a theoretical study

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Publication details

The article was received on 17 Jun 2008, accepted on 22 Jul 2008 and first published on 17 Sep 2008


Article type: Paper
DOI: 10.1039/B810220A
New J. Chem., 2009,33, 471-478

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    The unusual reactivity of benzene and monosubstituted benzenes towards tetracyanoethylene oxide: a theoretical study

    G. Jiménez-Osés, J. Elguero and J. I. García, New J. Chem., 2009, 33, 471
    DOI: 10.1039/B810220A

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