REACTION OF DILITHIUM BENZOPHENONE, DILITHIUM 9-FLUORENONE AND THE LITHIUM SALT OF BENZOPHENONE KETYL WITH CHLORIDES AND ANHYDRIDES OF CARBOXYLIC ACIDS

Article abstract of DOI:10.1016/S0022-328X(00)83502-0

The reaction of dilithium benzophenone and the lithium salt of benzophenone ketyl with anhydrides and chlorides of benzoic and acetic acid and the reaction of dilithium 9-fluorenone with acetic anhydride were investigated.In addition to the expected products Ar2C(COR)OCOR, products of the type Ar2C=CR(OCOR) were also obtained, and in the case of reactions with acetyl chloride and acetic anhydride, products of the type Ar2CH(OCOR).ESR studies showed that ketyl is formed in the reaction of dilithium benzophenone with acetic anhydride, and the ClDNP method revealed thatbenzhydryl acetate is formed, at least in part, by hydrogen transfer to a free radical produced by O-acetylation of the ketyl.The results suggest a competition between addition and electron transfer reactions.