6533b82bfe1ef96bd128d6ef
RESEARCH PRODUCT
Glycidyl Tosylate: Polymerization of a “Non‐Polymerizable” Monomer permits Universal Post‐Functionalization of Polyethers
Arthur D. ZieglerJan BlankenburgPhilipp JungHolger Freysubject
Ethylene oxidering-opening polymerization010405 organic chemistryCommunicationLeaving groupEpoxideGeneral Chemistry010402 general chemistry01 natural sciencesRing-opening polymerizationCommunicationsCatalysis0104 chemical scienceschemistry.chemical_compoundMonomerchemistryPolymerizationpolyetherPolymer chemistryCopolymerNucleophilic substitutionRing‐Opening Polymerizationfunctionalizationpoly(ethylene oxide)poly(propylene oxide)description
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 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-08-19 | Angewandte Chemie International Edition |