370 Royal Society : — 



The apparent dissimilarity of the two reactions would thus be 

 reduced to the unequal stability of the sulphocarbamic acids of the 

 amyle- and phenyle-series. 



" On New Nitrogenous Derivatives of the Phenyle- and Benzoyle- 

 series." By P. Griess, Esq. 



Piria's important discovery that the action of nitrous acid upon 

 asparagine gives rise to the formation of malic acid, has led to a very 

 general application of this agent in the study of nitrogenous sub- 

 stances. The results obtained have been almost always analogous 

 to those produced by Piria ; the reaction may be illustrated by the 

 following examples : — 



(C,H,0,)" I N + 2N03=H,0,+4N + (^« ^^^^ " 1 O,. 



. Malic acid. 



[' I N + N03 = HO + 2N+ ^1^ 2= I O,. 



Phenylamine. Phenol. 



The plan hitherto adopted consisted in submitting the aqueous 

 solution of the nitrogenous body directly to the action of nitrous 

 acid, or in dissolving the body in nitric acid, and passing into the 

 solution a current of biuoxide of nitrogen. By employing alcoholic 

 and ethereal solixtious, I have arrived at different results, establishing 

 a new mode of reaction ; of the facts which I have observed the fol- 

 lowing may be quoted as illustrations. 



Action of Nitrous Acid on Ficramic Acid. Diazodinitrophenol. 

 On passing a current of nitrous acid into an alcoholic solution of 

 picramic acid — 



c,,h,N30,„=c,Y(n6j,)o„ 



\H,N / 

 the red liquid assumes at once a yellow colour, and furnishes rapidly 

 a copious deposit of yellow crystals. No gas is evolved during the 

 reaction. The yellow crystals, purified by recrystallizatiou from 

 alcohol, are found to contain 



C,3H,N,0,„, 

 and are obviously formed according to the equation — 

 C„ H, N30,„ + N03=3H0 + C,, H, N, 0,„. 

 The new body, for which I propose the provisional name diazodi- 

 nitrophenol, is soluble in alcohol and ether, and crystallizes from the 

 former solvent in magnificent golden-yellow plates, which detonate 

 on heating. Acids have no action upon this substance ; on ebulli- 

 tion with water it appears to undergo decomposition ; alkalies induce 

 at once a copious evolution of gas, and give rise to the formation of 

 dinitrophenol. This metamorphosis appears to indicate that the 

 new body still belongs directly to the phenol-group ; the constitu- 



