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


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


High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene - Descarga este documento en PDF. Documentación en PDF para descargar gratis. Disponible también para leer online.

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





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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. View Full-Text

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





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

Fuente: http://mdpi.com/



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