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Synthesis and Ring Opening Polymerization of a New Functional Lactone, α-Iodo-ε-caprolactone: A Novel Route to Functionalized Aliphatic Polyesters.

A new functional lactone, α-iodo-ε-caprolactone (αIεCL), was synthesized from ε-caprolactone by anionic activation using a non-nucleophilic strong base (lithium diisopropylamide) followed by an electrophilic substitution with iodine chloride. Ring-opening (co)polymerizations of the resulting monomer with ε-caprolactone were carried out using tin 2-ethylhexanoate as a catalyst in toluene at 100 °C. Homopolymerization of αIεCL was achieved, and poly(αIεCL) was fully characterized by SEC, (1) H NMR and elemental analysis. Random copolymerizations of αIεCL with εCL were controlled with experimental molecular weights close to the theoretical values, narrow molecular weight distributions and a good agreement between experimental and theoretical molar compositions of αIεCL.