Preparation of Polymeric Analogs of N,N-Dichloro-p-Toluenesulfonamide and Their Use for Oxidation of Alcohols, Oxidative Lactonization of Diols, and Chlorination of Carbonyl Compounds

Insoluble polystyrenes containing sulfonamide moiety were prepared by copolymerization of p-styrenesulfonamide and divinylbenzene with AIBN. The polymers were treated with tert-butyl hypochlorite to afford the polystyrenes containing N,N-dichlorosulfonamide moiety. These functional polymers were used for oxidation of alcohols, oxidative lactonization of diols, and α-chlorination of carbonyl compounds. In most cases, the carbonyl compounds, the lactones, and the α-chlorocarbonyl compounds as the corresponding products were obtained in excellent yields. The spent polymer reagents could be separated from the reaction system by simple filtration, and could be fully regenerated without loss of activity.