Fluorinated beta-lactones and poly(beta-hydroxyalkanoate)s: synthesis via epoxide carbonylation and ring-opening polymerization

摘要

Efficient and mild reaction conditions were developed for the catalytic carbonylation of fluorinated epoxides to their corresponding beta-lactones. Six new lactones with fluorinated side chains were prepared in high isolated yields. These lactones were polymerized to form a series of new poly(beta-hydroxy-alkanoate)s with fluorinated side chains, and their properties were examined with respect to their hydrocarbon analogs. Finally, copolymerizations were performed with fluorinated lactones and beta-butyrolactone, which resulted in tapered copolymers rather than the expected random copolymers. (C) 2008 Elsevier Ltd. All rights reserved.