The Journal of Organic Chemistry

Decarboxylation and rearrangement of 3, 3-dialkyl-2-oxocarboxylic acids

N Rabjohn, CA Harbert

Index: Rabjohn,N.; Harbert,C.A. Journal of Organic Chemistry, 1970 , vol. 35, # 11 p. 3726 - 3729

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Citation Number: 3

Abstract

The thermal decomposition of 3, 3-dialkyl-2-oxocarboxylic acids (1) has been shown to lead to decarboxylation and rearrangement. Although 3, 3-dimethyl-2-oxobutyric acid (le) undergoes decarbonylation, 2-oxo acids with larger groups in the 3 position, la-d, afforded mixtures of ketones by 1, 2 shifts. Ethyl, butyl, and heptyl groups migrated with similar ease, lb, while phenyl was found to have essentially the same migratory aptitude as pentyl in 2- ...