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

Gérard Audran, Mitchell T. Blyth, Michelle L. Coote, Georg Gescheidt, Micael Hardy, Jeffrey Havot, Maxence Holzritter, Samuel Jacoutot, Jean Patrick Joly, Sylvain R. A. Marque, Tataye Moussounda Moussounda Koumba, Dmytro Neshchadin, Enzo Vaiedelich

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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. 

Original languageEnglish
Pages (from-to)6561-6576
Number of pages16
JournalOrganic Chemistry Frontiers
Volume8
Issue number23
DOIs
Publication statusPublished - 7 Dec 2021
Externally publishedYes

Keywords

  • Homolysis
  • mesolysis
  • alkoxyamines
  • chemical oxidation
  • photochemical

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