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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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Publication details

The article was received on 22 Nov 2012, accepted on 12 Dec 2012 and first published on 12 Dec 2012


Article type: Edge Article
DOI: 10.1039/C2SC22053A
Citation: Chem. Sci., 2013,4, 1092-1097
  • Open access: Creative Commons BY license
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    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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