Journal of the American Chemical Society

Electrophilic Substitution at Saturated Carbon. XXIII. Stereochemical Stability of Allylic and Vinyl Anions

DH Hunter, DJ Cram

Index: Hunter,D.H.; Cram,D.J. Journal of the American Chemical Society, 1964 , vol. 86, p. 5478 - 5490

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Citation Number: 36

Abstract

The potassium tert-butoxide catalyzed isomerization and hydrogen-isotope exchange reactions of cis-and trans-a-IIiethylstilbene and a-benzylstyrene, and of cis-and trans- stilbene, have been studied in tert-butyl alcohol and tert-butyl alcohol-0-d. The kinetics of deuterium incorporation and of isomerization of cis-and trens-a-methylstilbene and a- benzylstyrene into one another can be made most internally consistent with a mechanism ...