156 



hepoet— 1900. 



As in the similai* cases of isatin and carbostyril, the chemical evidence 

 leaves the question of the constitution of o-oxycarbanil itself undecided. 

 On the one hand, its formation by the distillation of o-aminophenyl 

 ethyl carbonate is most easily explained on the assumption that it has the 



Scale of Oscillation Frequencies. 



■3 § 



^ o 



"o '^ 



s s 



" s 



I-t o 



bo ^3 



« I-l 



^ o 



^ 2 



- Ph 



Lactam or ketouio ether. o-Oxycarbanil. 



Curves of Molecular Vibration. 



Lactim or enolic ether. 



ketonic or lactam constitution, and that the reaction takea place according 

 to the equation 



C.H<<g.H5.oc,H, = CA<gf>CO + C,H.-OH. 



This view is supported by the fact that it forms a v\^ell-defined compound 

 with phenylhydrazine.i On the other hand, its direct formation from the 

 lactim ether by the action of hydrochloric acid seems to point to the 

 enolic or lactim structure as being the more probable. It is, however, 

 now generally admitted that arguments based on chemical reactions are 

 inconclusive in cases such as that under consideration, where shifting of a 

 hydrogen atom may easily take place. 



' Bender,^Zoc. cit. 



