Glycidyl Tosylate: Polymerization of a "Non-Polymerizable" Monomer permits Universal Post-Functionalization of Polyethers.
Angew Chem Int Ed Engl, 2019/9/09;58(37):12883-12886.
Jung P[1], Ziegler AD[1], Blankenburg J[1, 2], Frey H[1]
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PMID: 31339633DOI: 10.1002/anie.201904203
Impact factor: 16.823
Abstract
Glycidyl tosylate appears to be a non-polymerizable epoxide when nucleophilic initiators are used because of the excellent leaving group properties of the tosylate. However, using the monomer-activated mechanism, this unusual monomer can be copolymerized with ethylene oxide (EO) and propylene oxide (PO), respectively, yielding copolymers with 7-25 % incorporated tosylate-moieties. The microstructure of the copolymers was investigated via in situ 1 H NMR spectroscopy, and the reactivity ratios of the copolymerizations have been determined. Quantitative nucleophilic substitution of the tosylate-moiety is demonstrated for several examples. This new structure provides access to a library of functionalized polyethers that cannot be synthesized by conventional oxyanionic polymerization.
Keywords: functionalization; poly(ethylene oxide); poly(propylene oxide); polyether; ring-opening polymerization
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