Sodium perborate, secondary oxidant

All classes of primary amine (including primary, secondary, and tertiary alkyl as well as aryl) are oxidized to nitro compounds in high yields with dimethyl dioxirane." Other reagents that oxidize various types of primary amines to nitro compounds are dry ozone, various peroxyacids," MeRe03/H202,"" Oxone ," ° tcrt-butyl hydroperoxide in the presence of certain molybdenum and vanadium compounds, and sodium perborate." ... 

A -Arylimincs (21a) can be oxidatively rearranged to fonnamides (21b) with sodium perborate.42 The reaction works best for secondary or aryl R groups. An oxaziridine intermediate is proposed. Results with chiral secondary R groups indicate epimeriza-tion, suggested to occur via equilibration of (21a) with its enamine tautomer. 

Dimethyldioxirane in wet acetone oxidizes isocyanates to nitro compounds (RNCO —> RN02). Oximes can be oxidized to nitro compounds with peroxytri-fluoroacetic acid, or Oxone , sodium perborate, among other ways. Secondary hydroxylamines are also oxidized to nitrones with Mn02 in dichloromethane. " Primary and secondary alkyl azides have been converted to nitro compounds by treatment with PhsP followed by ozone.Aromatic nitroso compounds are easily oxidized to nitro compounds by many oxidizing agents. OS III, 334 V, 367, 845 VI, 803 81, 204. 

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