314 



Mr Ruhemann, The Action of Acidchlorides, etc. 



This fact, already, supports the constitution of the red isomeride 

 C 14 H 12 3 , and the following behaviour points to the same con- 

 clusion. Under the influence of phenylhydrazine, the compound 

 yields a phenylhydrazone which, on account of its insolubility in 

 alkalis, is to be represented thus : 



C fi H 5 NH.N:C.CH.C 6 H 5 

 C.CH 3 

 CO.C.CO.CH3; 



its formation, therefore, is accompanied by the change of the 

 enolic into the ketonic grouping. Analogous compounds are 

 formed by the action of semicarbazide and hydroxylamine on 

 the red substance C 14 H 12 3 ; these are to be expressed by the 

 symbols : 



NH 2 . CO . NH . N : C — CH . C 6 H 5 



\ 



C . CH 3 ; resp. 



CO— C . CO . CH 3 



OH . N : C— CH . C fi H, 



C . CH 3 

 CO— C . CO . CH, 



The circumstance that the latter two compounds are colourless 

 leads to the conclusion that the red colour of C 14 H 12 3 is due to 

 the enolic group, 



COH : C— 

 CO— 

 and disappears with the change into the ketonic grouping, 



CO— CH— 



CO— 



This behaviour of the red isomeride allows of a ready explanation 

 of the results at which Claisen and Ewan arrived in the course of 

 their study of oxalyldibenzylketone. This substance forms yellow 

 as well as blue salts. From the properties of the red compound, 

 C 14 H 12 3 , and triethyl oxalylaconitate it follows that the latter 

 salts are to be formulated thus : 



Me'. O.C = C.C 6 H 5 



\ 



C . OMe' 



OC— C.C fi H, 



