Influence of nucleophiles on the high-temperature aqueous isomerization of cis-to trans-cinnamic acid

GA Reed, DR Dimmel, EW Malcolm

Index: Reed, Gregg A.; Dimmel, Donald R.; Malcolm, Earl W. Journal of Organic Chemistry, 1993 , vol. 58, # 23 p. 6364 - 6371

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Citation Number: 13

Abstract

The rate of isomerization of cis-to trans-cinnamic acid in water at 195" C was monitored as a function of added nucleophile. The expected nucleophile addition products were not observed but could be synthesized and, when subjected to the reaction conditions, rapidly converted to trans-cinnamic acid. Deuterium labeling studies indicated that proton abstraction was not the rate-determining step, that the a-deuterium of a, P-dideuterio-cis- ...

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