Endo selectivities of some methyl-substituted dienophiles in Diels-Alder reactions with cyclopentadiene
01 Nov 1970-Journal of the American Chemical Society (American Chemical Society)-Vol. 92, Iss: 22, pp 6548-6553
About: This article is published in Journal of the American Chemical Society.The article was published on 1970-11-01. It has received 105 citations till now. The article focuses on the topics: Cyclopentadiene.
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TL;DR: In this paper, a line of distinction between the mechanistic alternatives for the Diels-Alder reaction was drawn, considering all experimental and theoretical criteria, for one-step and two-step reactions.
Abstract: The question of concerted or consecutive bond formation arises in all types of cycloaddition reactions. Stereochemical investigations and studies of regiospecificity as well as intensive kinetic investigations with regard to substituent and solvent effects, and the dependence of the reaction on temperature and pressure permit in many cases mechanistic conclusions concerning the Diels-Alder reaction. Efforts towards a theoretical interpretation, ab initio and semiempirical calculations, the application of frontier molecular orbital theory (FMO) as well as thermochemical measurements permit a description of the energy hypersurface of these [4+2]-cycloadditions. An attempt is made here to draw a line of distinction between the mechanistic alternatives—one-step reaction versus two-step reaction—considering all experimental and theoretical criteria.
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