Acyclic β-Phosphonylated Nitroxides: A New Series of Counter-Radicals for “Living”/Controlled Free Radical Polymerization
Macromolecules2000Vol. 33(4), pp. 1141–1147
Citations Over TimeTop 10% of 2000 papers
Sandra Grimaldi, Jean‐Pierre Finet, François Le Moigne, Abdelhamid Zeghdaoui, Paul Tordo, Didier Benoit, Michel Fontanille, Yves Gnanou
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.
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