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Ring-opening metathesis polymerization of cyclooctene derivatives with chain transfer agents derived from glycerol carbonate

Abstract : The synthesis of a variety of mono- and di-(glycerol carbonate) telechelic polyolefins has been achieved upon ruthenium-catalyzed ring-opening metathesis polymerization (ROMP) of cyclooctene (COE) derivatives in the presence of a vinyl or acryloyl derivative of glycerol carbonate (GC) acting as a chain-transfer agent (CTA). Reaction monitoring based on SEC and 1H NMR analyses suggested that the ROMP proceeds through the formation of first the α-GC,ω-vinyl-poly(cyclooctene) (PCOE) intermediate, which eventually evolves over time into the α,ω-di(GC)-PCOE. The nature of the solvent was shown to have a significant impact on both the reaction rates and the eventual selectivity for the mono-/di-telechelic PCOE. ROMP of 3-alkyl (methyl, ethyl, n-hexyl)-substituted COEs (3-R-COEs) afforded only the α-GC,ω-vinyl-poly(3-R-COE)s, as a result of the steric hindrance around the active intermediate, while a 5-ethyl substituted COE (5-Et-COE) enabled access to the corresponding α,ω-di(GC)-poly(5-Et-COE). The ROMP of 5,6-epoxy-, 5-hydroxy- and 5-oxo-functionalized COEs in the presence of acryloyl-GC as the CTA has also been achieved, affording from the first two monomers polymers with GC end-groups at both extremities, while a 60 : 40 mixture of mono- and di-GC terminated P(5-O[double bond, length as m-dash]COE) was observed in the latter case.
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Submitted on : Tuesday, August 26, 2014 - 10:26:17 AM
Last modification on : Thursday, March 5, 2020 - 2:05:02 PM
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Abdou K. Diallo, Liana Annunziata, Stéphane Fouquay, Guillaume Michaud, Frédéric Simon, et al.. Ring-opening metathesis polymerization of cyclooctene derivatives with chain transfer agents derived from glycerol carbonate. Polymer Chemistry, Royal Society of Chemistry - RSC, 2014, 5 (7), pp.2583-2591. ⟨10.1039/C3PY01639K⟩. ⟨hal-01058100⟩

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