Solvent-free macrocyclisation by nucleophile-mediated oxa-Michael addition polymerisation of divinyl sulfone and alcohols
- Resource Type
- Authors
- Christian Slugovc; Simone Strasser; Christina Wappl
- Source
- Polymer Chemistry. 8:1797-1804
- Subject
- chemistry.chemical_classification
Addition reaction
Polymers and Plastics
010405 organic chemistry
Chemistry
Organic Chemistry
Bioengineering
Polymer
010402 general chemistry
01 natural sciences
Biochemistry
Divinyl sulfone
0104 chemical sciences
chemistry.chemical_compound
Polymerization
Nucleophile
Yield (chemistry)
Michael reaction
Organic chemistry
Organic synthesis
- Language
- ISSN
- 1759-9962
1759-9954
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.