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1. Ring-opening polymerization of [epsilon]-caprolactone catalyzed by sulfonic acids: computational evidence for bifunctional activation

Author

Susperregui, Nicolas, Delcroix, Damien, Martin-Vaca, Blanca, Bourissou, Didier, and Maron, Laurent

Subjects
Catalysis -- Analysis, Lactones -- Structure, Lactones -- Chemical properties, Methane -- Chemical properties, Methanol -- Chemical properties, Polymerization -- Analysis, Biological sciences, Chemistry
Abstract

The mechanism of ring-opening of [epsilon]-caprolactone by methanol catalyzed by trifluoromethane and methane sulfonic acids is analyzed, where the sulfonic acid has behaved as a bifunctional catalyst. The ring-opening has involved the cleavage of the endo C-O bond of the tetrahedral intermediate with concomitant proton transfer, where the sulfonic acid has acted as a proton shuttle via its acidic hydrogen atom and basic oxygen atoms.

Published
2010

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