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Modified Poly(ε-caprolactone)s: An Efficient and Renewable Access via Thia-Michael Addition and Baeyer–Villiger Oxidation

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journal contribution
posted on 13.05.2014 by Matthias Winkler, Yasmin S. Raupp, Lenz A. M. Köhl, Hanna E. Wagner, Michael A. R. Meier
The preparation of a novel class of ε-caprolactone (CL) monomers, modified at the β-position of the ester function, is described. The efficient thia-Michael addition to cyclohex-2-en-1-one and subsequent Baeyer–Villiger oxidation provided the regioselectively modified CL monomers. To enable a sustainable Baeyer–Villiger oxidation, several reaction procedures were investigated. In order to test a controlled ring-opening polymerization of the prepared monomers, the kinetics were studied and the monomer to initiator ratios were varied in order to prepare poly­(ε-caprolactone)­s with different molecular weights and different side groups.