Summary: Novel polyester and copolyesters have been prepared by anionic ring‐opening polymerization of racemic 4‐alkyloxycarbonyl‐3,3‐dimethyl‐2‐oxetanones that had been synthesized in five steps from diethyl oxalpropionate used as chemical precursor. The anionic polymerizations, realized in bulk or in solution with tetraethylammonium benzoate as initiator, led to a homopolymer and copolymers with high molecular weights and polydispersity indices close to unity. These features can be explained by the presence of two methyl groups on the same carbon atom in the lactone, preventing transfer reactions to the monomer. Preparation of seeds and re‐initiation by addition of fresh monomer confirmed a living process. The hydrolysis of poly[(R,S)‐3,3‐dimethylmalic acid] under physiological conditions yielded (R,S)‐3,3‐dimethylmalic acid. A terpolymer was also prepared for biological studies related to its use as biodegradable materials for tissue regeneration.Structure of poly[(R,S)‐3,3‐dimethylmalic acid].imageStructure of poly[(R,S)‐3,3‐dimethylmalic acid].
Abstract-Novel ®,® 0 ,¯-trisubstituted¯-lactones have been prepared by a concise and ef cient synthesis in ve steps from commercial racemic diethyl oxalpropionate. These lactones with different lateral groups can be polymerized or co-polymerized for obtaining polyesters with high molecular weight. Chemical modi cation of these functionalized hydrolyzable polymers will be used to adjust their properties to the selected temporary applications.
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