Intramolecular addition of oxyradicals to benzene rings: a DFT study

Bucher, G. (2011) Intramolecular addition of oxyradicals to benzene rings: a DFT study. Collection of Czechoslovak Chemical Communications, 76(8), pp. 947-956. (doi: 10.1135/cccc2011042)

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The reactivity of a series of oxyradicals related to the triplet state of β-phenylpropiophenone was investigated by density functional theory. Analysis of the potential energy hypersurfaces indicates that radical addition to the β-phenyl ring should occur with a smaller barrier than intramolecular hydrogen abstraction from the benzylic position, although the latter reaction is far more exothermic. Addition can occur in <i>ipso</i>- and <i>ortho</i>-position of the β-phenyl ring, with ortho addition being slightly more favourable. As both addition reactions are predicted to be mildly exothermic and exergonic, intermolecular trapping of the resulting cyclohexadienyl- type radicals should be feasible

Item Type:Articles
Keywords:Ab initio calculations, density functional calculations, radical reactions, cyclicization
Glasgow Author(s) Enlighten ID:Bucher, Dr Goetz
Authors: Bucher, G.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Collection of Czechoslovak Chemical Communications
Publisher:Institute of Organic Chemistry and Biochemistry
Published Online:07 July 2011

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