Fundamental Studies on Molecular Design for Specialty Polymeric Materials by Ring-Opening Polymerization of Heterobicyclic Compounds

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1. Synthesis and Ring-Opening Polymerization of Novel Bicyclic OxalactamsTwo new bicyclic oxalactams, 2-oxa-5-azabicyclo[2.2.2]octan-6-one (2,5-BOL) and 2-oxa-6-aza-bicyclo[2.2.2]octan-5-one (2,6-BOL) were synthesized and their ring-opening polymerizabilities were examined. 2,5-BOL was anionically polymerized to give a polyamide having cis-2,5-linked tetrahydropyran rings in the main chain. 2,6-BOL did not undergo anionic polymerization, and afforded only a dimeric adduct in a low yield. In contrast, 2,6-BOL was easily polymerized with cationic initiators to give oligoethers containing 6-membered lactam rings in the main chain.2. Synthesis of Polyesters Having Tetrahydropyran Rings in their Main ChainsThree 2,6-dioxabicyclo[2.2.2]octan-3-one derivatives having an ester group at 4-position were newly prepared. These monomers underwent cationic polymerization to produce polyesters having 2,5-linked tetrahydropyran rings in their backbones and the corresponding ester groups as the side chains. These polyesters showed much improved solubilities compared with the parent polyester. Hydrolysis of these polyesters were examined at 30 ﾟC in a buffer solution at pH 7.2.