Oxidative Halo-Decarboxylation of α,β-Unsaturated Carboxylic Acids

Article abstract of DOI:10.1021/jo00092a009

A procedure for oxidative halo-decarboxylation of α,β-unsaturated carboxylic acids using iodosylbenzene, or iodosylbenzene diacetate, and N-chloro-, N-bromo-, or N-iodosuccinimide is presented.Good yields of the corresponding bromoalkenes are obtained when the α,β-unsaturated carboxylic acids are substituted with an aromatic substituent in the β-position and N-bromosuccinimide is used as the halogenation reagent.The scope of mainly the oxidative bromo-decarboxylation reaction is presented, and a tentative mechanism is proposed.