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The stereochemistry of the Alder-Ene reaction between 2,3,3-trimethyl-1-butene and maleic anhydride

✍ Scribed by Louis E. Friedrich; J.A. Kampmeier; Maureen Good

Publisher: Elsevier Science
Year: 1971
Tongue: French
Weight: 213 KB
Volume: 12
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)96979-5

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✦ Synopsis

Most workers assume that the simple ene reaction' involves a concerted mechanism with the same syn-syn stereochemistry as the familiar Diels-Alder reaction. Actually, however, only those stepwise reactions involving initial hydrogen or proton transfer from the ene to the enophile are rigorously eliminated by the complete migration of the double bond of propene-l-Cl4 in the reaction with maleic anhydride. Qualitative transfer of asymmetry from ene to adduct leads to the same general conclusion.4

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