Activation of carbonyl bonds by quaternary ammoniums and a (Na+:crown-ether) complex: investigation of the ring-opening polymerization of cyclic esters
Literature Information
Publication Date
2013-04-03
DOI
10.1039/C3PY00304C
Impact Factor
5.582
Authors
Anne Milet, Frédéric Peruch, Brigitte Bibal
View Original
Abstract
Quaternary ammoniums associated with bis(trifluoromethane)sulfonimide (NTf2) or tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BARF) counterions were readily prepared from commercially available tertiary amine, amidine, guanidine and pyridine. As predicted by molecular modelling, these ammonium salts proved to be efficient multiple H-bond donor catalysts in the ring-opening polymerization of cyclic esters (lactide, δ-valerolactone and ε-caprolactone). In addition, a sodium(I) complex of [15-c-5] crown-ether paired with NTf2 or BARF was shown to activate the cyclic monomers through a cation–dipole interaction. These simple and non-protonated ionic structures appeared as attractive alternative organocatalysts to classical H-bond donors for the activation of carbonyl bonds.
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Source Journal
Polymer Chemistry
CiteScore:
8.6
Self-citation Rate:
7.3%
Articles per Year:
457
Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.
Recommended Compounds
6-amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
CAS Number:
6642-31-5
Molecular Formula:
C6H9N3O2
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