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Epr Studies On Electron Transfer Reactions Between O-Benzoyl-N-Alkylhydroxylamines and Perfluoroacyl Peroxides. Generation of n- and sec-Alkyl Perfluoroacyl Nitroxides and sec- and tert-Alkyl Perfluoroalkyl Nitroxides

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Both EPR studies and product analysis have disclosed that the oxidation of O-benzoyl-N-alkylhydroxylamines (1, 4, 7) by perfluoroacyl peroxides (2) is an electron transfer-initiated process. Depending on the nature of the alkyl groups in the substrates, the caged radical pair CP1 (RN*OCOPh, RfCOO*) may react through different radical pathways resulting in different nitroxides along with the neutral products. With primary, benzyl and secondary alkyl groups, a 1,2-acyl shift becomes the predominant pathway resulting in acyl nitroxides (3, 5). With tert-alkyl groups such as tert-butyl, tert-alkyl perfluoroalkyl nitroxides (8) are formed via β-scission of both RN*OCOPh and RfCOO*. A general mechanistic pathway is proposed for the titled reactions generating the quite useful fluorinated nitroxides.

Affiliations: 1: Department of Chemistry Huazhong University of Science and Technology Wuhan 430074, CHINA


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