Anionic alternating copolymerization of a bifunctional six‐membered lactone and glycidyl phenyl ether: Selective synthesis of a linear polyester having lactone moiety

Abstract

AbstractAn imidazole‐initiated copolymerization of an aromatic bislactone, 10‐methyl‐2H,8H‐benzo[1,2‐b:5,4‐b′]bipyran‐2,8‐dione (1), and glycidyl phenyl ether (GPE) was investigated. In spite of the bifunctional nature of 1 that would potentially permit formation of networked and thus insoluble polymers upon its copolymerization, only one of the two lactone moieties of 1 exclusively underwent the copolymerization to give a linear polyester. Spectroscopic analysis of the polyester and its reductive scission into the corresponding fragment revealed that the polyester was formed by a 1:1 alternating copolymerization of GPE and the lactone moiety of 1. The other lactone in 1 that did not participate in the copolymerization was quantitatively incorporated into the side chain of the polyester as a reactive site, of which ring‐opening reactions by amine and alcohol as nucleophilic reagents allowed chemoselective polymer reactions. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 1661–1672, 2009