Acyclic β-phosphonylated nitroxides: a new series of counter-radicals for 'living'/controlled free radical polymerization

Sandra Grimaldi, Jean Pierre Finet, François Le Moigne, Abdelhamid Zeghdaoui, Paul Tordo, Didier Benoit, Michel Fontanille, Yves Gnanou

Research output: Contribution to journalArticlepeer-review

215 Scopus citations

Abstract

Oxidation of α-(N-alkylamino) phosphonic acid esters, carrying one or two alkyl groups as substituents on their α-carbon, by m-chloroperbenzoic acid afforded the corresponding stable β-phosphonylated nitroxides. The nitroxides derived from α-mono-tert-butyl α-alkylaminophosphonic acid esters are stable compounds despite the presence of a hydrogen atom on the α-carbon bound to the nitroxyl group. The ESR study of these nitroxides in solution showed that this β-hydrogen atom lies in the nodal plane to the nitroxyl function. These β-phosphonylated nitroxides were found to efficiently control the free radical polymerization reaction of styrene, with a much faster rate of propagation than that observed in TEMPO-mediated systems.

Original languageEnglish (US)
Pages (from-to)1141-1147
Number of pages7
JournalMacromolecules
Volume33
Issue number4
DOIs
StatePublished - Jan 1 2000

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this