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Issue 3, 2013
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Benzyl bispidine as an efficient replacement for (−)-sparteine in ring opening polymerisation

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Abstract

The synthesis and application of a dibenzyl-functionalized bispidine, in combination with 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) co-catalyst, has been demonstrated to be an excellent catalyst for the controlled ring-opening polymerisation (ROP) of lactide and cyclic carbonate monomers. Notably, the polymerisation proceeds with negligible transesterification or epimerisation, with the polymerisation of stereopure L-lactide affording highly crystalline poly(lactide) with a Tm of 156 °C. ROP of racemic lactide results in the observation of a modest degree of stereocontrol such that the probability of isotactic enchainment, Pm = 0.74. Comparison of a range of alternative hydrogen bond donor co-catalysts revealed that TU displayed the highest polymerisation rates in combination with the dibenzyl-functionalized bispidine.

Graphical abstract: Benzyl bispidine as an efficient replacement for (−)-sparteine in ring opening polymerisation

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Supplementary files

Article information


Submitted
22 Nov 2012
Accepted
12 Dec 2012
First published
12 Dec 2012

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2013,4, 1092-1097
Article type
Edge Article

Benzyl bispidine as an efficient replacement for (−)-sparteine in ring opening polymerisation

R. Todd, G. Rubio, D. J. Hall, S. Tempelaar and A. P. Dove, Chem. Sci., 2013, 4, 1092
DOI: 10.1039/C2SC22053A

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