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Treatment of aromatic nitro compounds with metal hydrides gives good yields of azo compounds. For example, one could use: Lithium aluminium hydride [20] Zinc metal with sodium hydroxide. [19] (Excess zinc will reduce the azo group to a hydrazino compound.)
Zinin reaction or Zinin reduction involves reduction of nitro aromatic compounds to the amines using sodium sulfide. [1] It is used to convert nitrobenzenes to anilines. [2] [3] The reaction selectively reduces nitro groups in the presence of other easily reduced functional groups (e.g., aryl halides and C=C bonds) are present in the molecule.
The Béchamp reduction is broadly applicable to aromatic nitro compounds. [4] [5] Aliphatic nitro compounds are however more difficult to reduce, often remaining as the hydroxylamine. Tertiary aliphatic nitro compounds, however, are converted in good yield to the amine using the Béchamp reduction. [6] The reduction proceeds in a multistep manner.
Nitrogen derivates such as amides, nitriles, imines, and most other organonitrogen compounds are reduced to the corresponding amines. Nitroarenes can be converted to azoxyarenes, azoarenes, or hydroazoarenes, depending on the reaction conditions. [1] Some common functional group reductions using SMEAH can be found below:
Nitro compounds participate in several organic reactions, the most important being reduction of nitro compounds to the corresponding amines: RNO 2 + 3 H 2 → RNH 2 + 2 H 2 O. Virtually all aromatic amines (e.g. aniline) are derived from nitroaromatics through such catalytic hydrogenation.
The intermediate imine can be isolated or reacted in-situ with a suitable reducing agent (e.g., sodium borohydride) to produce the amine product. [2] Intramolecular reductive amination can also occur to afford a cyclic amine product if the amine and carbonyl are on the same molecule of starting material. [4]
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Nitro compounds may be reduced to either the hydroxylamine or amine oxidation level with samarium(II) iodide, depending on the conditions employed. Electron transfer, followed by proton transfer and elimination generates an intermediate nitroso compound, which undergoes two more rounds of electron transfer and protonation to afford the ...