Generation of α-aminoxylcarbenium ions by electron-transfer oxidation of N-tert-butyl-3-phenyloxazirane and their role in nitrone spin trapping chemistry

Abstract

Using low-temperature EPR and optical absorption spectroscopy the α-aminoxylcarbenium ion 1˙⁺ was directly observed in frozen (77 K) halogenated matrices as a result of electron-transfer oxidation of N-tert-butyl-3-phenyloxazirane 4 by matrix radical cations. The aminoxylcarbenium ion 1˙⁺ reacts with nucleophilic anions Cl^– to form an α-chloro-substituted aminoxyl radical 3.