2 AKT. 18. M. KUHAEA : MOLECULAK 



quantity of the acid chloride suffices to transform smoothly a large 

 quantity of the N-ether into the corresponding substituted acid 

 amide by its catalytic action, and also that an attempt to isolate 

 the intermediate product or products ended in a negative result. 

 Lately, llo^Yever, the author has succeeded in isolating benzyl- 

 benzimido-chloride, CgH,^ • C CI : N • C'H.^ • CgH.^, as an intermediate 

 product of the rearrangement of N-benzylbenzaldoxime by the 

 action of phosphorus pentachloride, and in converting the chloride 

 into benzylbenzamide, CeHg . CO • NH . CHo • CoH^ , by the action 

 of water, and he is now able to put forward an explanation of the 

 above molecular rearrangement, based upon the assumption that a 

 hypothetical dichloro-substitution product is first formed, which, 

 immediately parts with hydrochloric acid and yields benzylbenz- 

 imido-chloride as the intermediate product, this being followed 

 by the formation of benzylbenzamide by the action of water. 

 The change is evidently analogous, in part, to the molecular 

 rearrangement of ketoxiraes, as may be seen from the following 

 scheme : 



It appears, therefore, highly probable that the molecular 

 rearrangement of N-benzylbenzaldoxime by the action of an acid 

 chloride, such as acetyl chloride, is due to the formation of the 

 same intermediate product, benzylbenzimido-chloride, which is in- 

 stantly changed into benzylbenzamide by the action of acetic acid 



