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Glycidyl Tosylate: Polymerization of a "Non-Polymerizable" Monomer permits Universal Post-Functionalization of Polyethers.

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.

SUBMITTER: Jung P

PROVIDER: S-EPMC6771516 | biostudies-other | 2019 Sep

REPOSITORIES: biostudies-other

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Glycidyl Tosylate: Polymerization of a "Non-Polymerizable" Monomer permits Universal Post-Functionalization of Polyethers.

Jung Philipp P Ziegler Arthur D AD Blankenburg Jan J Frey Holger H

Angewandte Chemie (International ed. in English) 20190819 37

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 <sup>1</sup> H NMR spectroscopy, and the reactivit ...[more]

PMID: 31339633

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