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Issue 14, 2018
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Reinvestigation of the mechanism of polymerization of β-butyrolactone from 1,5,7-triazabicyclo[4.4.0]dec-5-ene

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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

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Publication details

The article was received on 06 Feb 2018, accepted on 03 Mar 2018 and first published on 05 Mar 2018


Article type: Paper
DOI: 10.1039/C8PY00206A
Citation: Polym. Chem., 2018,9, 1840-1847
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    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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