66 ELECTROLYSIS AND ELECTROS YN THE SIS 



In a third paper 1 Gattermann applies this reduction 

 to a large number of compounds which for lack of 

 space cannot here be enumerated. The nature of the 

 reaction is the same in all cases. The esters of the 

 carboxylic acids show the same behavior as the acids 

 themselves. 



These reduction products have all become the sub- 

 jects of patents. 2 



Lob and Gattermann have produced direct and in- 

 direct evidence that the amido-phenols are actually 

 formed by the molecular rearrangement of phenyl- 

 hydroxylamine, which occurs as an intermediate 

 product. 



Lob 3 has found that p- and o-chlor-aniline are ob- 

 tained by the electrolytic reduction of nitro-benzene 

 suspended in fuming hydrochloric acid, nitro-benzene 

 dissolved in alcoholic hydrochloric acid, and nitro- 

 benzene dissolved in mixtures of hydrochloric and 

 acetic acid. With hydrobromic acid the correspond- 

 ing brom-anilines are formed. 



The reaction takes place as shown in the following 

 equations: 



2. C 6 H 6 NHOH+ HCl = C 6 H 6 NHCl+H a O 



1 Chem. Ber., 2J, 1927. 



* German Patent, 75260 and additions to the same, 



3 Ztschr. f. Elektrochem., 3, 46. 



