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

  1. Jiménez-Osés, G. 1
  2. Elguero, J. 2
  3. García, J.I. 1
  1. 1 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

  2. 2 Instituto de Química Médica
    info

    Instituto de Química Médica

    Madrid, España

    ROR https://ror.org/02vznxv75

Zeitschrift:
New Journal of Chemistry

ISSN: 1144-0546

Datum der Publikation: 2009

Ausgabe: 33

Nummer: 3

Seiten: 471-478

Art: Artikel

DOI: 10.1039/B810220A SCOPUS: 2-s2.0-61849083148 WoS: WOS:000263922500004 GOOGLE SCHOLAR

Andere Publikationen in: New Journal of Chemistry

Institutionelles Repository: lockOpen Access Editor

Zusammenfassung

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.