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Issue 11, 2017
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Solvent-free macrocyclisation by nucleophile-mediated oxa-Michael addition polymerisation of divinyl sulfone and alcohols

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Abstract

The oxa-Michael addition reaction has been widely studied and employed in organic synthesis, but has not been developed as a tool for polymer synthesis. Herein, the 4-dimethylaminopyridine initiated polyaddition reaction of divinyl sulfone and several di- or multifunctional alcohols has been studied. This atom-economical polymerisation reaction proceeds quickly and quantitatively under solvent-free conditions producing predominantly macrocyclic products following a zwitter-ionic mechanism. Multifunctional alcohols yield duroplastic polymers. Considering the ready availability of alcohols, the oxa-Michael addition polymerisation is an interesting alternative to the well-established thiol-Michael addition polymerisation.

Graphical abstract: Solvent-free macrocyclisation by nucleophile-mediated oxa-Michael addition polymerisation of divinyl sulfone and alcohols

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Supplementary files

Article information


Submitted
24 Jan 2017
Accepted
16 Feb 2017
First published
16 Feb 2017

This article is Open Access

Polym. Chem., 2017,8, 1797-1804
Article type
Paper

Solvent-free macrocyclisation by nucleophile-mediated oxa-Michael addition polymerisation of divinyl sulfone and alcohols

S. Strasser, C. Wappl and C. Slugovc, Polym. Chem., 2017, 8, 1797
DOI: 10.1039/C7PY00152E

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