129 



CH 3 



I 

 C 



CH a 

 I 

 C 



-> HC CC1 



I II 



HC CH 



HC CC1 



I II 



HC CH 



C — CO — CH 3 C — COOH 



o-chlorop- acetyl toluene o-chloro-p-toluic acid 



The mechanism of the change from isocarvoxime to carvoline is 

 now no longer explained by Wallach by accepting a Beckmann's 

 re-arrangement; on the contrary, he rather considers the 

 first-named reaction an explanation of the latter. For the 

 mutual exchange of the radicals CH 3 and OH would for example 

 fail in the case of cyclic oximes, if the exchange of radicals is not 

 taken as purely schematic. But if, on the other hand, the inter- 

 mediary formation of a nitrogenous ring is considered as the first 

 phase of the reaction: 



CEC-CH, CKC-t-CH, 



NOH 



acetoxime 



N' 



+ H 2 



which in the second phase is again opened in another direction, 

 forming now a more stable system: 



CH3COH CH 3 CO 



II -> II 



N-CH 3 NHCH 3 



methylacetamide 



the interpretation of all the changes is entirely uniform. In the 

 presence of only aromatic radicals, the re-arrangement by means of 

 phosphorus chloride is explained by the following graphic formulae 



oxime 



A\ 



NOH 





\y 



N- 



+ HC1 



'■i\ 



NCI 



CC1 



N- 

 imide chloride. 



