OF AROMATIC COMPOUNDS. 67 



3. C,H 6 NHC1 = 



NH, 



^CC1 and HC 



I II I UNIVERSIT 



NH. 



H 



Cl 



The phenyl-chloramine formed by the action of 

 hydrochloric acid on phenyl-hydroxylamine changes, 

 by molecular rearrangement, into o- and p-chlor- 

 aniline. 



Gattermann 1 has obtained direct proof of the inter- 

 mediate formation of phenyl-hydroxylamine by adding 

 benzaldehyde to the solution at the beginning of the 

 electrolysis. He was thus able to isolate a condensa- 

 tion product of phenyl-hydroxylamine with benzalde- 

 hyde. In this way he obtained benzylidene-phenyl- 

 hydroxylamine, 



O 



C.H 6 N- -CH,C 6 H 6 , 



from nitre-benzene ', benzy lidene-o-tolyl-hydroxylamine, 



C 6 H 6 .CH - N.C 6 H 6 .CH 8 , 



from o-nitro-toluene, and the corresponding benzyl- 

 idene compounds from m-nitro-toluene, p-nitro-toluene, 

 nitro-p-xylene, and m-nitro-benzoic acid. 



The presence of formaldehyde in the electrolytic 

 1 Chem. Ber., 29, 3040. 



