Facile and Selective Deallylations of Esters under ‘Aqueous’ Free-Radical Conditions

Abstract

The conversion of allyl esters into carboxylic acids using radical initiators has been achieved in high yields in aqueous media.

Key words

deallylation - esters - radical - selective - aqueous

References and Notes

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17

Authors are grateful to the referees for the suggestion of a plausible mechanism and valuable insight into the kinetics of the acyl radicals.

22

Competition experiments with a 1:1 mixture of the methyl ester and allyl ester of 2-(4-isobutylphenyl)propanoic acid (Table [2] , entry 4) under our general reaction conditions revealed no consumption of the methyl ester. The corresponding acid, formed by reaction at the allyl ester, was formed in 86% and 91% in benzene and H₂O, respectively.