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STEREOCHEMICAL ASPECTS OF THE DIELS-ALDER REACTION,
CALIFORNIA INST OF TECH PASADENA GATES AND CRELLIN LABS OF CHEMISTRY
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In the Diels-Alder reaction of hexachlorocyclopentadiene and alpha-methyl-styrene, the cistrans ratio of deuterium in the beta-position of the alkene remains unchanged in the adduct. The reactions of cis- and trans-1,2-dichloroethylene with cyclopentadiene have been found to be at least 99.5 stereospecific. Since these systems were designed to favor the diradical intermediate which might be involved in a two-step mechanism, the observed high degree of specificity is best accounted for on the basis of a concerted, one-step mechanism. Author
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