SYNTHESIS AND CATIONIC POLYMERIZATION OF A NOVEL OPTICALLY-ACTIVE VINYL ETHER WITH L-PROLINE STRUCTURE

Synthesis and cationic polymerization of a novel vinyl ether with an L -proline moiety, N-carbobenzoxy-L-proline 2-vinyloxyethyl ether (ZProV E), were carried out. ZProVE was prepared by the condensation of N-car bobenzoxy-L-proline and 2-hydroxyethyl vinyl ether. Cationic polymeriz ation of ZProVE was carried out in dichloromethane at -50, -20 degrees C, or room temperature. The number-average molecular weight ((M) over bar(n)) of the polymer obtained in the polymerization at -50 degrees C was 44900, and the [alpha](D)(23) value of the polymer was -36.1 deg rees, which was somewhat larger (more positive) than that of ZProVE (- 46.4 degrees). Cationic copolymerizations of ZProVE and isobutyl vinyl ether proceeded readily to afford the corresponding copolymers. Alkal ine hydrolysis of poly(ZProVE) afforded poly(hydroxyethyl vinyl ether) .