title: Chemically triggered C-ON bond homolysis of alkoxyamines. Quaternization of the alkyl fragment.
abstract: The C-ON bond homolysis in alkoxyamine 2a can be chemically triggered by the protonation of the 4-pyridylalkyl fragment. The resulting 15-fold increase in k(d) (Chem. Commun. 2011, 47, 4291-4293) was investigated experimentally and theoretically by quaternization of the pyridyl moiety using methylating (MeOTs), acylating (AcCl), and benzylating (PhCH(2)Br) agents as well as by oxidation of the pyridyl moiety into N-oxide and by the formation of a dative bond with BH(3) as a Lewis acid.
authors.affiliation: Laboratoire Chimie Provence UMR 6264 - CNRS, Université de Provence, case 521, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France. paul.bremond@univ-provence.fr
authors.forename: Paul
authors.initials: P
authors.lastname: Brémond
authors.forename: Abdoulaye
authors.initials: A
authors.lastname: Koïta
authors.forename: Sylvain R A
authors.initials: SR
authors.lastname: Marque
authors.forename: Vincent
authors.initials: V
authors.lastname: Pesce
authors.forename: Valérie
authors.initials: V
authors.lastname: Roubaud
authors.forename: Didier
authors.initials: D
authors.lastname: Siri