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Molecules 2000, 5(12), 1417-1428; doi:10.3390/51201417

Article

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

Davor Margetic* , Martin R. Johnston and Ronald N. Warrener

Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia

* Author to whom correspondence should be addressed.

Received: 3 November 2000 / Accepted: 6 November 2000 / Published: 22 December 2000

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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.

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

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