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Issue 2, 2015
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Oxa-Michael addition polymerization of acrylates catalyzed by N-heterocyclic carbenes

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Abstract

N-heterocyclic carbenes (NHCs) catalyze the oxa-Michael addition polymerization of hydroxyl functionalized acrylate monomers. This polymerization smoothly proceeded at room temperature to produce poly(ester-ether)s, which include new polymers having alicyclic, alkene, and alkyne groups in the main chain. The post polymerization modification of the alkene-functionalized polymer using thiol–ene “click” chemistry is demonstrated. The structure of poly(2-hydroxyethyl acrylate) was analyzed in detail by NMR and ESI-MS analyses and methanolysis, thus allowing estimation of the frequency of the transesterification. The NHC catalyst was covalently linked to the C terminal of the polymer chain, indicating that the NHC acts as a Lewis base to generate the zwitterionic intermediate without directly activating the hydroxyl groups of the monomers.

Graphical abstract: Oxa-Michael addition polymerization of acrylates catalyzed by N-heterocyclic carbenes

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Publication details

The article was received on 26 Aug 2014, accepted on 11 Sep 2014 and first published on 11 Sep 2014


Article type: Paper
DOI: 10.1039/C4PY01184H
Citation: Polym. Chem., 2015,6, 294-301
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    Oxa-Michael addition polymerization of acrylates catalyzed by N-heterocyclic carbenes

    S. Matsuoka, S. Namera and M. Suzuki, Polym. Chem., 2015, 6, 294
    DOI: 10.1039/C4PY01184H

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