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

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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MDPI and ACS Style

Margetic, D.; Johnston, M.R.; Warrener, R.N. High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene. Molecules 2000, 5, 1417-1428.

AMA Style

Margetic D, Johnston MR, Warrener RN. High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene. Molecules. 2000; 5(12):1417-1428.

Chicago/Turabian Style

Margetic, Davor; Johnston, Martin R.; Warrener, Ronald N. 2000. "High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene." Molecules 5, no. 12: 1417-1428.

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