88 PROCEEDINGS OF THE AMERICAN ACADEMY 



taiued from our attempts to oxidize or saponify the biomtrinitrophe- 

 nyltartrouic ester, we thought that perhaps the anilido comjjound 

 might behave better, and accordingly the following experiments were 

 made, in the hope (unfortunately not realized) of decomposing the 

 anilidotrinitropheuyltartronic ester into substances which would con- 

 firm our inferences in regard to its nature. The substance was al- 

 lowed to stand in the cold with an aqueous solution of potassic 

 permanganate, but, although a considerable part of it disapj^eared, 

 no organic oxidation product could be detected. In the hope of sa- 

 ponifying the ester, we added to it an excess of sodic hydrate dissolved 

 in water, and allowed the reddish brown solution thus formed to stand 

 in a corked flask at ordinary temperatures for some weeks. During 

 this standing a strong odor of phenylisocyanide was developed, and, 

 if the amount of ester was small, the color changed to yellow ; if, on 

 the other hand, the quantity was large, it retained its dark brown color ; 

 at the end of the experiment, nothing was obtained except a brown 

 precipitate of most unpromising appearance, formed by adding an acid 

 to the solution, and the phenylisocyanide already mentioned as recog- 

 nized by its smell. As the formation of this substance would neces- 

 sitate a complete destruction of the benzol ring which carried the 

 nitro groups and malonic ester radical, we did not think it worth 

 while to repeat the experiment. 



This formation of an isocyanide from the destruction of a benzol 

 ring containing nitro groups by means of an aqueous solution of sodic 

 hydrate recalls the work of Post and Hiibncr,* who found that ordi- 

 nary dinitrobenzol when boiled with a solution of sodic or potassic 

 hydrate was decomposed with formation of a cyanide quickly if the 

 solution was strong, slowly if it was dilute. They also found that 

 picric acid behaved in the same way, thus confirming the earlier ob- 

 servation of Wohler.f 



A n ilidotrin itroph enjjJmalon ic Este r, 

 CoHlCcH.NH) (N0J3CII(C00C JI^).. 



This substance was made to see whether it would be possible b.y 

 treatment with nitric acid to convert it directly into either its nitrite 

 or the anilidotartronic ester described above. It was found, however, 

 that standing for several days at ordinary temperatures with strong 

 nitric acid produced complete decomposition of part of the substance, 

 the only product insoluble in the acid being unaltered anilidotrinitro- 



* T5cr. d. cli. G., V. 408 (1872). t Pogg. Ann., XIII. 488 (1828), 



