Radical polymerization behavior of a vinyl substituted cyclic carbonate, 4-phenyl-5-vinyl-1,3-dioxoran-2-one (1), is described. Radical polymerization of 1 proceeded through selective vinyl polymerization to produce polymers bearing carbonate groups in the side chain, in contrast to that of an oxirane analogue of 1, 1-phenyl-2-vinyl oxirane that proceeds via the selective ring-opening fashion. Although the homopolymerization of 1 produce polymers in relatively lower yield, copolymerizations effectively provided cyclic carbonate-containing copolymers. Nucleophilic addition of primary amines to the resulting homopolymers and copolymers produced the corresponding multifunctional polymers. (C) 2004 Wiley Periodicals, Inc.