The chemical and enzymatic hydrolyses of 1,1-diethoxycarbonyl-2-vinylcyclopropane (1) were investigated. The product of the pig liver esterase (PLE)-catalyzed hydrolysis of 1 is a chiral trans monoester of 2-vinylcyclopropane dicarboxylic acid. New 1,1-disubstituted 2-vinylcyclopropane monomers (2a,b) were synthesized by the esterification of this ester. Methylated beta -cyclodextrin was used to complex monomers 2a,b, yielding water-soluble 1:1 host/guest complexes. These complexes were polymerized in aqueous media by a free radical ring-opening mechanism.