Studies in decarboxylation. Part VI. A comparison of the transition states for the decarboxylation of β-keto-and βγ-unsaturated acids

DB Bigley, JC Thurman

Index: Bigley,D.B.; Thurman,J.C. Journal of the Chemical Society [Section] B: Physical Organic, 1968 , p. 436 - 440

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Citation Number: 7

Abstract

The effect of substituents on the rate of thermal decarboxylation of βγ-unsaturated acids is compared to their effect on the decarboxylation of β-keto-acids. From the close similarity observed, it is argued that the reactions have nearly identical transition states. It is demonstrated that the transition state for the olefinic acids is largely non-polar; by analogy, the keto-acids are concluded to decarboxylate through a largely non-polar mechanism. ...