Web Release Date: March 17,
Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters
and
IBM Almaden Research Center, 650 Harry Road, San Jose, California 95120, Kenyon College, Gambier, Ohio 43022, and Department of Chemistry, Stanford University, Stanford, California 95032
Received February 3, 2006
Abstract:
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) is an effective organocatalyst for acyl transfer as well as the ring-opening polymerization of cyclic esters. Its high activity is attributed to its ability to simultaneously activate both esters and alcohols, as demonstrated in a model reaction. This unique mechanism makes TBD a remarkably simple example of a bifunctional catalyst. The simplicity of the reaction conditions, the ready commercial availability of the catalyst, and its high activity provide an accessible methodology to allow future studies of tailor-made polyesters.
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