In acid solution, amines are obtained, in alkaline solution, azoxy, azo and hydrazo compounds, and in neutral solution hydroxylamino compounds.
They may also be obtained by the reduction of nitroso compounds and of hydrazo compounds and of hydrazones (J.
They may be prepared by the reduction of nitro compounds in alkaline solution (using zinc dust and alkali, or a solution of an alkaline stannite as a reducing agent); by oxidation of hydrazo compounds; or by the coupling of a diazotized amine and any compound of a phenolic or aminic type, provided that there is a free para position in the amine or phenol.
By oxidizing agents they are converted into azoxy compounds, and by reducing agents into hydrazo compounds or amines.
It melts at 112-114° C. and is easily reduced to the corresponding hydrazo compound.
Those not containing a nitro group may be prepared by the oxidation of the corresponding mixed hydrazo compounds with mercuric oxide.
In this latter case hydrazo-benzene C 6 H 5 NH NH C 6 H 5 is first formed and then undergoes a peculiar re-arrangement into benzidine (see H.
The Benzidine and Semidine Change.-Aromatic hydrazo compounds which contain free para positions are readily converted by the action of acids, acid chlorides and anhydrides into diphenyl derivatives; thus, as mentioned above, hydrazobenzene is converted into benzidine, a small quantity of diphenylin being formed at the same time.
If, however, one of the para positions in the hydrazo compound is substituted, then either diphenyl derivatives or azo compounds are formed, or what is known as the semidine change takes place (P. Jacobson, Berichte, 1892, 2 5, p. 99 2; 1893, 26, p. 681; 1896, 29, p. 2680; Annalen, 1895, 287, p. 97; 1898, 3 0 3, p. 290) A para mono substituted hydrazo compound in the presence of a hydrochloric acid solution of stannous chloride gives either a para diphenyl derivative (the substituent group being eliminated), an ortho-semidine, a para-semidine, or a diphenyl base, whilst a decomposition with the formation of amines may also take place.