Homolysis/mesolysis of alkoxyamines activated by chemical oxidation and photochemical-triggered radical reactions at room temperature
Literature Information
Publication Date
2021-10-14
DOI
10.1039/D1QO01276B
Impact Factor
5.281
Authors
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
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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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-(2-Aminoethyl)-1H-isoindole-1,3(2H)-dione hydrochloride (1:1)
CAS Number:
30250-67-0
Molecular Formula:
C10H11ClN2O2
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