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The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.
The Béchamp reduction (or Béchamp process) is a chemical reaction that converts aromatic nitro compounds to their corresponding anilines using iron as the reductant: [1] 4 C 6 H 5 NO 2 + 9 Fe + 4 H 2 O → 4 C 6 H 5 NH 2 + 3 Fe 3 O 4. This reaction was once a major route to aniline, but catalytic hydrogenation is the preferred method. [2]
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.
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.
Nitroso compounds can be prepared by the reduction of nitro compounds [1] or by the oxidation of hydroxylamines. [2] Ortho-nitrosophenols may be produced by the Baudisch reaction. In the Fischer–Hepp rearrangement, aromatic 4-nitrosoanilines are prepared from the corresponding nitrosamines.
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 ...
For textile dying, a typical nitro coupling partner would be disodium 4,4′-dinitrostilbene-2,2′-disulfonate. Typical aniline partners are shown below. Typical aniline partners are shown below. Since anilines are prepared from nitro compounds, some azo dyes are produced by partial reduction of aromatic nitro compounds.
In organic synthesis the Béchamp reaction is used for producing arsonic acids from activated aromatic substrates. The reaction is an electrophilic aromatic substitution, using arsenic acid as the electrophile. The reaction proceeds according to this idealized stoichiometry for the preparation of arsanilic acid: [1]