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High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene

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Author(s): Davor Margetic | Martin R. Johnston | Ronald N. Warrener

Journal: Molecules
ISSN 1420-3049

Volume: 5;
Issue: 12;
Start page: 1417;
Date: 2000;
Original page

Keywords: cycloaddition | inverse electron-demand | o-benzoquinones | ab initio and DFT calculations

ABSTRACT
Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-π-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products.
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