NEF. — BIVALENT CARBON. 181 



by boiling fulminate of mercury with water. Among the manj for- 

 mula' which have been advanced as representing the constitution of 

 this acid, the one proposed by Steiner,* 



CN-CHNO2 

 I 

 HOC : NH, 



possesses the greatest probability. It explains very simply the forma- 

 tion of nitroacetonitrile, CN— CH2NO2, from it by means of sulphuric 

 acid,t as well as the formation of trinitroacetonitrile, CN— C (N02)3 5 

 by means of sulphuric acid and nitric acid, t 



It follows directly from the above experiments, that, on boiling mer- 

 curic fulminate with water and either ammonic chloride or potassic 

 chloride, an addition of water or of hydrogen chloride to the unsatu- 

 rated carbon atom present in this salt must at first take place, and 

 thus the products 



hgON : C ^ and hgON : C ^ 



must be formed. These can then act further, in the second stage, on 

 unchanged mercuric fulminate in exactly the same way as formyl- 

 chloridoxime acts on sodic fulminate (see above). It was therefore 

 suspected for a long time that cyanisonitrosoacethydroxamic acid 

 must be an intermediate product in the formation of fulminuric acid 

 (its isomer). After, however, many fruitless attempts were made to 

 convert this substance into fulminuric acid, by oxidation, by boiling 

 with mercuric oxide, or with ammonia and oxide of mercury, etc.. it 

 seems to me impossible that this is formed as an intermediate product. 

 If fulminic acid is identical with nitrocyanacetamide, 



CN-CHNOo 

 I 

 HOC : NH, 



and this is proved to be the case farther on, it must be formed 

 from mercury fulminate in a manner entirely analogous, for instance, 

 to the formation of mesoxanilide from phenylisocyanide, phosgene, 

 and water, § or also to that of cyanisonitrosoacethydroxamic acid 

 from formylchloridoxime and soluble fulminic acid salts. The fol- 

 lowing explanation of the reaction which takes place in the formation 



* Ber. d. chem. Ges., IX. 784. 



t Steiner, Ber. d. chem. Ges., IX. 782. 



t Schisclikoff, Ann. de Chim. et de Phys., [3.], XLIX. 310. 



§ Ann. Chem. (Liebig), CCLXX. 291. 



