Glycidyl tosylate: polymerization of a “non-polymerizable” monomer permits universal post-functionalization of polyethers
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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 1H 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.
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Angewandte Chemie : International edition, 58, 37, Wiley-VCH, Weinheim, 2019, https://doi.org/10.1002/anie.201904203