p-Styrenesulfinic Acid and Its Polymer as Reactants

Abstract The free-radical aqueous polymerizations of p-styrenesulfinates (Na, K, NH4, NHEt3-salts) provided watersoluble polymers with high molecular weights at low conversions. The polymers contained 62–84% of the sulfinate unit and indicated half-oxidation potentials ranging from 340 to 415 mV. The nucleophilic reactions of the sodium polysulfinate [poly(sulfinic acid)] prepared from cross-linked polystyrene are highly dependent upon the swelling nature of the solvent. The reactions consisting of (A) simple displacements with activated halomethyl groups, (B) reductive additions to quinonoid compounds such as TCNQ and alizarin, and (C) displacements of the activated aromatic nitro groups, e.g., of 2,4,7-trinitrofluorenone have been investigated and the results compared with those of p-toluene and p-styrenesulfinates. The effect of the solvent on the reaction rate is in the order: DMSO>DMF>HMPA.