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Article Dans Une Revue Journal of Organic Chemistry Année : 2016

C-ON Bond Homolysis of Alkoxyamines, Part 11: Activation of the Nitroxyl Fragment

Gérard Audran
  • Fonction : Auteur
Paul Brémond
  • Fonction : Auteur
Toshihide Yamasaki
  • Fonction : Auteur

Résumé

A few years ago, Bagryanskaya and colleagues (J. Org. Chem. 2011) showed that protonation of the nitroxyl fragment deactivated the alkoxyamine C-ON bond. Conversely, our group showed that protonation (Chem. Commun. 2011), as well as other chemical reactions such as oxidation or amine quaternization (Org. Lett. 2012), of the pyridyl moiety carried by the alkyl fragment was suitable to activate the homolysis of the C-ON bond. To pursue our goal of applying alkoxyamines as theranostic agents (Org. Biomol. Chem. 2014 and Mol. Pharmaceutics 2014) by activation of the C-ON bond homolysis, we turned our interest to the chemical activation of the nitroxyl fragment by oxidation/reduction of selected functions. Conversion of a hydroxyl group located close to the nitroxyl moiety successively into aldehyde, then acid, and eventually into ester, led to a successive decrease in k(d).

Domaines

Chimie
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Dates et versions

hal-01408190 , version 1 (03-12-2016)

Identifiants

Citer

Gérard Audran, Paul Brémond, S.R.A. Marque, Toshihide Yamasaki. C-ON Bond Homolysis of Alkoxyamines, Part 11: Activation of the Nitroxyl Fragment. Journal of Organic Chemistry, 2016, 81 (5), pp.1981-1988. ⟨10.1021/acs.joc.5b02790⟩. ⟨hal-01408190⟩
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