Reactions of peroxides: II. Reaction of carboxylic acids with iodine and peroxides

Aroyl peroxides andt-butylperoxy isopropyl carbonate decarboxylate aliphatic carboxylic acids in the presence of iodine to form iodides in high yields. The aroyl peroxides also abstract carboxylic acid hydrogen from aromatic and perfluorocarbon acids. A proposed scheme is presented for the reaction of aroyl peroxides with carboxylic acids illustrating homolytic decarboxylation as taking place in an equilibrium between a pair of acyloxy radicals. These radicals are derived from the peroxide and acid and maintained in association by hydrogen bonding and iodine complexation. Presented at the AOCS Meeting, Washington, D.C., March 1968. ARS, USDA.