Studies in decarboxylation. Part 10. Effect of β-substituents on the rate of gas-phase decarboxylation of βγ-unsaturated acids

Abstract

The large rate enhancements in the gas-phase decarboxylation of βγ-unsaturated acids resulting from substitution of the β-carbon atom are shown to be derived from increased nucleophilicity of the γ-carbon atom. This being so, the carboxylic hydrogen atom must be transferred as an electrophile, and the direction of the other electron movements is thereby implied.