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

Simone Strasser, Christina Wappl, Christian Slugovc

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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.
Original languageEnglish
Pages (from-to)1797-1804
JournalPolymer Chemistry
Issue number8
Publication statusPublished - 16 Feb 2017

Fields of Expertise

  • Advanced Materials Science

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