Abstract
This chapter provides a review of nitro compounds, azides, and related compounds. The chapter first discusses aliphatic nitro compounds: nitroalkanes, nitroalkenes, nitroso compounds, nitroxyl radicals, alkylhydroxylamines, azoxy and azo compounds, hydrazines, and nitric acid esters. Primary and secondary nitroalkanes are reducible electrochemically in acid and neutral solution. The reduction of a nitroalkane, in acidic medium at low temperature at a mercury electrode, produces the corresponding alkyl-hydroxylammonium salt as the main product in a four-electron reaction. Some amine and carbonyl compound may also be formed. As the alkylhydroxylamine is not further reducible under acidic conditions, it is suggested that the amine is formed through a tautomerization of the intermediate nitroso compound into the oxime. The oxime may then either be reduced to amine, or hydrolyzed to a carbonyl compound. The chapter also describes aromatic nitro compounds. Polarography of nitrobenzene in acid solution shows a four-electron wave, followed by a wave at a more negative potential with a height approximately corresponding to a two-electron reduction. In alkaline solution the latter wave is not observed.
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