Zinin reaction

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.

Reaction mechanism and example

The reaction requires water. Thiosulfate is one product. A possible stoichiometry for the reaction is:

4 ArNO₂   +   6 S^2-   + 7 H₂O → 4  ArNH₂   +   3 S₂O₃^2- + 6 OH^-

Mechanistic studies have implicated a role for disulfide that is generated in situ. Nitrosobenzenes (ArNO) and phenylhydroxylamine (ArNHOH) are probable intermediates.^[4]

Dinitrobenzenes can often be reduced selectively to the nitroaniline. ^[5]

History

The reaction was discovered by a Russian organic chemist Nikolay Zinin (Russian: Николай Николаевич Зинин) (25 August 1812, Shusha – 18 February 1880, Saint Petersburg).

References

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