Issue 23, 2021

Homolysis/mesolysis of alkoxyamines activated by chemical oxidation and photochemical-triggered radical reactions at room temperature

Abstract

Alkoxyamines, which are connected with a phenol moiety by a (substituted) methylene bridge undergo homolytic cleavage upon chemical oxidation or a photo-induced hydrogen transfer. This selectively triggered reaction yields a nitroxide radical. In the presence of an excess of lead dioxide as the oxidant in tert-butylbenzene as solvent, spontaneous, instantaneous and almost quantitative generations of nitroxides from various alkoxyamines are observed at room temperature, which support activation energies for the cleavage lower than 100 kJ mol−1. The rate and the amount of released nitroxide depend on the amount of “catalyst” and the structure of alkoxyamines.

Graphical abstract: Homolysis/mesolysis of alkoxyamines activated by chemical oxidation and photochemical-triggered radical reactions at room temperature

Supplementary files

Article information

Article type
Research Article
Submitted
25 Aug 2021
Accepted
01 Oct 2021
First published
14 Oct 2021
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2021,8, 6561-6576

Homolysis/mesolysis of alkoxyamines activated by chemical oxidation and photochemical-triggered radical reactions at room temperature

G. Audran, M. T. Blyth, M. L. Coote, G. Gescheidt, M. Hardy, J. Havot, M. Holzritter, S. Jacoutot, J. Joly, S. R. A. Marque, T. M. M. Koumba, D. Neshchadin and E. Vaiedelich, Org. Chem. Front., 2021, 8, 6561 DOI: 10.1039/D1QO01276B

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