Preparation and Free-Radical Polymerizations of Methyl-4-vinylphenylsulfoxide and Methyl-4-vinylbenzylsulfoxide

Methyl-4-vinylphenylsulfoxide (1) was prepared by the selective oxidation of 4-methylthiostyrene with sodium metaperiodate in 87% yield. This monomer was readily homopolymerized in DMSO by AIBN at 60°C. The polymer obtained is soluble in ethanol, chloroform, DMSO, and DMF, but insoluble in water, benzene, and petroleum ether. The inherent viscosity of this polymer was 0.33 dL/g in DMSO. This sulfoxide monomer (1) was copolymerized with styrene, methyl methacrylate, acrylo-nitrile, and acrylamide under radical conditions. From the copolymerization with styrene, copolymerization parameters were obtained as follows; r1 = 0.56, rSt, = 0.26, and Q1 = 1.19, e1 = 0.58. Similarly, methyl-4-vinylbenzylsulfoxide (2) was prepared, and the polymerizability of (2) was also investigated.