Issue 14, 2018

Reinvestigation of the mechanism of polymerization of β-butyrolactone from 1,5,7-triazabicyclo[4.4.0]dec-5-ene

Abstract

The questionable mechanism initially proposed to explain how 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) allows us to ring-open β-lactones, such as β-butyrolactone (BL), is reinvestigated here. With the use of a trisubstituted β-lactone, i.e. (R,S)-benzylcarbonyl-3,3-dimethyl-2-oxetanone, and the association of techniques such as 1H/DOSY NMR and MALDI/ESI-MS, we demonstrated that BL is effectively polymerized by the TBD in bulk at 60 °C, minorly from the reported N-acyl-α,β-unsaturated TBD species, and majorly from crotonate anions issued from the basic activation of BL. In contrast to what has been reported, the TBD is not covalently linked to the PBL chain but mainly plays the role of a counterion in the –C(O)O, TBDH+ active site.

Graphical abstract: Reinvestigation of the mechanism of polymerization of β-butyrolactone from 1,5,7-triazabicyclo[4.4.0]dec-5-ene

Supplementary files

Article information

Article type
Paper
Submitted
06 Feb 2018
Accepted
03 Mar 2018
First published
05 Mar 2018

Polym. Chem., 2018,9, 1840-1847

Reinvestigation of the mechanism of polymerization of β-butyrolactone from 1,5,7-triazabicyclo[4.4.0]dec-5-ene

S. Moins, C. Henoumont, J. De Winter, A. Khalil, S. Laurent, S. Cammas-Marion and O. Coulembier, Polym. Chem., 2018, 9, 1840 DOI: 10.1039/C8PY00206A

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