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2010-02-08 - Article/Dans un journal avec peer-review - Anglais - 13 page(s)

Debuigne A., Poli Rinaldo, De Winter Julien , Pascal Laurent, Gerbaux Pascal , Dubois Philippe , Wathelet J-P., Jerome Ch., Detrembleur Christophe, "Cobalt-mediated radical coupling (CMRC): an unusual route to mid-chain-functionalized symmetrical macromolecules" in Chemistry, 16, 6, 1799-1811

  • Edition : John Wiley & Sons (United Kingdom)
  • Codes CREF : Chimie macromoléculaire (DI1315), Catalyses hétérogène et homogène (DI1334), Chimie organique (DI1313)
  • Unités de recherche UMONS : Matériaux Polymères et Composites (S816), Synthèse et spectrométrie de masse organiques (S836)
  • Instituts UMONS : Institut de Recherche en Science et Ingénierie des Matériaux (Matériaux)
Texte intégral :

Abstract(s) :

(Anglais) Cobalt-mediated radical coupling (CMRC) is a straightforward approach to the synthesis of symmetrical macromolecules that relies on the addition of 1,3-diene compounds onto polymer precursors preformed by cobalt-mediated radical polymerization (CMRP). Mechanistic features that make this process so efficient for radical polymer coupling are reported here. The mechanism was established on the basis of NMR spectroscopy and MALDI-MS analyses of the coupling product and corroborated by DFT calculations. A key feature of CMRC is the preferential insertion of two diene units in the middle of the chain of the coupling product mainly according to a trans-1,4-addition pathway. The large tolerance of CMRC towards the diene structure is demonstrated and the impact of this new coupling method on macromolecular engineering is discussed, especially for midchain functionalization of polymers. It is worth noting that the interest in CMRC goes beyond the field of polymer chemistry, since it constitutes a novel carbon–carbon bond formation method that could be applied to small organic molecules.

Notes :
  • (Anglais) Lecture en ligne: http://onlinelibrary.wiley.com/doi/10.1002/chem.200902618/pdf
  • (Anglais) Publié en ligne le 28 décembre 2009
Identifiants :
  • DOI : 10.1002/chem.200902618