BIPHASE AND TRIPHASE CATALYSIS. ARSONATED POLYSTYRENES AS CATALYSTS IN THE BAEYER-VILLIGER OXIDATION OF KETONES BY AQUEOUS HYDROGEN PEROXIDE.

Article abstract of DOI:10.1021/ja00517a025

Arsonated polystyrene resins, prepared by a novel procedure, proved to be versatile catalysts for the Baeyer-Villiger oxidation of ketones by hydrogen peroxide. The insoluble beads of the catalyst can be quantitatively separated from the reaction mixture and recycled. Extensive hydrolysis of the lactone and ester products is prevented. In solvents miscible with aqueous hydrogen peroxide (biphase system), the catalysts facilitate oxidation of medium size cycloalkanones (C//4-C//7) and their alkyl and aryl derivatives, steroid ketones, and branched-chain aliphatic ketones. Larger size cycloalkanones, acetophenone, and straight-chain aliphatic ketones react very slowly or not at all. The arsonated polystyrene beads are effective catalysts and phase transfer agents in solvents immiscible with aqueous hydrogen peroxide. This represents the first example of triphase catalysis in oxidations by hydrogen peroxide.