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dc.contributor.authorAfarinkia, Kamyar*
dc.contributor.authorBearpark, M.J.*
dc.contributor.authorNdibwami, A.*
dc.date.accessioned2009-02-11T14:53:16Z
dc.date.available2009-02-11T14:53:16Z
dc.date.issued2003en
dc.identifier.citationAfarinkia, K., Bearpark, M. J., Ndibwami, A. (2003) A Computational and Experimental Investigation of the Diels-Alder Cycloadditions of Halogen Substituted 2(H)-pyran-2-one. The Journal of Organic Chemistry. 68 (19): 7158-7166.en
dc.identifier.urihttp://hdl.handle.net/10454/2366
dc.descriptionNoen
dc.description.abstract4-Chloro-2(H)-pyran-2-one undergoes thermal Diels−Alder cycloaddition with electron-deficient dienophiles to afford, without any significant selectivity, 6-endo- and 5-endo-substituted bicyclic lactone cycloadducts. In contrast to 3- and 5-bromo-2(H)-pyran-2-one, 4-chloro-2(H)-pyran-2-one does not undergo thermal cycloadditions with electron-rich dienophiles. The regio- and stereochemical preferences of the cycloadditions of 4-chloro-2(H)-pyran-2-one and other related 2(H)-pyran-2-ones are investigated computationally. Calculations were carried out on the transition states leading to the four possible regio- and stereoisomeric cycloadducts using density functional theory (B3LYP/6-31G*). These studies allow prediction of the regio- and stereoselectivity in these reactions which are in line with experimental observations.
dc.language.isoenen
dc.subjectComputationalen
dc.subjectDiels-Alder Cycloadditionsen
dc.subject4-Chloro-2(H)-pyran-2-oneen
dc.subjectElectron-deficient dienophilesen
dc.subjectStereoselectivityen
dc.subjectDensity functional theoryen
dc.titleA Computational and Experimental Investigation of the Diels-Alder Cycloadditions of Halogen Substituted 2(H)-pyran-2-oneen
dc.status.refereedYesen
dc.typeArticleen
dc.type.versionNo full-text in the repositoryen
dc.identifier.doihttps://doi.org/10.1021/jo0348827


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