Sodium perborate 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. 

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." ... 

Sodium perborate, NaBOa dlljO (mp 60 °C dec), is used for oxidations of primary aromatic amines to azo compounds [795] or nitro compounds [194] and of sulfides to sulfoxides and sulfones [794]. This reagent does not affect alcohols and only slightly affects alkenes [794]. 

The dehydrogenation of primary amines into azo compounds is achieved by sodium perborate, which converts A -acetyl-p-phenylenedi-amine into /3,p -diacetamidoazobenzene in 58% yield on heating at 50-60 °C with boric acid and acetic acid for 6 h [193],... 

The oxidation of aromatic primary amines to the corresponding azo compound with sodium perborate (equation 23) was first described by Mehta and Vakilwala in 1952. 

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