Sodium permanganate primary amines

In a related reaction, primary aromatic amines have been oxidized to azo compounds by a variety of oxidizing agents, among them Mn02, lead tetraacetate, O2 and a base, barium permanganate, and sodium perborate in acetic acid, tert Butyl hydroperoxide has been used to oxidize certain primary amines to azoxy compounds. 

The popularity of the Nef reaction is due in part to the ready availability of nitro compounds. Primary and secondary halides react with sodium nitrite in dimeAyl sulfoxide (DMSO) or dimethylform-amide (DMF) to give useful yields of nitro compounds. Primary amines can be oxidized to nitro compounds with potassium permanganate, m-chloroperbenzoic acitP or ozone. Chlorination of oximes with hypochlorous acid and reduction with magnesium, zinc or hydrogen/lpalladium gives secondary nitro compounds. Stabilized carbanions can be nitrated by treauitent with a nitrate ester, and enol acetates are nitrated by acetyl nitrate to give nitro ketones. ... 

Dissolving 3-aryl(alkyl)-1,2,4,5-tetrazines (21) in liquid ammonia or primary aliphatic amines at — 35°C to — 40°C, followed by addition of potassium permanganate, gives 6-alkylamino-3-aryl-(alkyl)-1,2,4,5-tetrazines (23) in reasonable to excellent yields. This shows that, under the reaction conditions, addition of A-nucleophiles to the tetrazine ring must have occurred (Scheme 1) <8 JHC123>. The presumption of a 1,6-dihydro intermediate (22) rests on the experimental result that tetrazines can be transformed by sodium borohydride into the isolable 1,6-dihydro-1,2,4,5-tetrazines, which can be considered as neutral homoaromatic systems <8UOC2i38>. 

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