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Communication
Controlled ROP of β-Butyrolactone Simply Mediated by Amidine, Guanidine, and Phosphazene Organocatalysts
Article first published online: 13 AUG 2012
DOI: 10.1002/marc.201200410
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Jaffredo, C. G., Carpentier, J.-F. and Guillaume, S. M. (2012), Controlled ROP of β-Butyrolactone Simply Mediated by Amidine, Guanidine, and Phosphazene Organocatalysts. Macromol. Rapid Commun., 33: 1938–1944. doi: 10.1002/marc.201200410
Publication History
- Issue published online: 9 NOV 2012
- Article first published online: 13 AUG 2012
- Manuscript Revised: 17 JUL 2012
- Manuscript Received: 8 JUN 2012
Keywords:
- beta-lactone;
- organocatalysis;
- poly(3-hydroxybutyrate);
- ring-opening polymerization
Abstract
Basic organocatalysts of the guanidine (1,5,7-triazabicyclo[4.4.0]dec-5-ene, TBD), amidine (1,8-diazabicyclo[5.4.0]-undec-7-ene, DBU), and phosphazene (2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2diazaphosphorine, BEMP) type do effectively polymerize β-butyrolactone (BL). Poly(3-hydroxybutyrate)s (PHBs) with controlled molecular features, that is, controlled molar masses, narrow molar mass distributions, and well-defined functional end groups are thus formed at 60 °C from bulk monomer, with 
up to 21 500 g mol−1. The formation of α,ω-guanidine/amidine/phosphazene,crotonate functionalized PHBs, as demonstrated by NMR, SEC, and MALDI–ToF mass spectrometry analyses, mechanistically suggests the formation of N-acyl-α,β-unsaturated propagating species that originate from 1:1 guanidine/amidine/phosphazene:BL adducts.