Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization.

Autor: Lepage ML; Stratingh Institute for Chemistry, Advanced Research Center Chemical Building Blocks Consortium (ARC CBBC), University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands., Alachouzos G; Stratingh Institute for Chemistry, Advanced Research Center Chemical Building Blocks Consortium (ARC CBBC), University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands., Hermens JGH; Stratingh Institute for Chemistry, Advanced Research Center Chemical Building Blocks Consortium (ARC CBBC), University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands., Elders N; Department Resin Technology, Akzo Nobel Car Refinishes BV, Rijksstraatweg 31, 2171 AJ Sassenheim, The Netherlands., van den Berg KJ; Department Resin Technology, Akzo Nobel Car Refinishes BV, Rijksstraatweg 31, 2171 AJ Sassenheim, The Netherlands., Feringa BL; Stratingh Institute for Chemistry, Advanced Research Center Chemical Building Blocks Consortium (ARC CBBC), University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2023 Aug 09; Vol. 145 (31), pp. 17211-17219. Date of Electronic Publication: 2023 Jul 27.
DOI: 10.1021/jacs.3c04314
Abstrakt: Butenolides are a class of 5-membered lactones that hold great potential as bio-based monomers to replace oil-derived acrylates, of which they are cyclic analogues. Despite this structural resemblance, the reactivity of the unsaturated ester moiety of electron-poor butenolides leans toward that of maleic anhydride, another essential monomer that does not homopolymerize but copolymerizes in a highly alternating fashion with polarized electron-rich comonomers. By studying the reactivity of 5-methoxy and 5-acyloxy butenolides through a combination of kinetics and density functional theory (DFT) experiments, we explain why electron-poor butenolides constitute a missing link between acrylates and maleic anhydride in radical polymerization.
Databáze: MEDLINE
Externí odkaz: