C-ON Bond Homolysis of Alkoxyamines, Part 11: Activation of the Nitroxyl Fragment - Aix-Marseille Université Access content directly
Journal Articles Journal of Organic Chemistry Year : 2016

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

Gérard Audran
  • Function : Author
Paul Brémond
  • Function : Author
Toshihide Yamasaki
  • Function : Author

Abstract

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).
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Dates and versions

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

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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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