NEF. — BIVALENT CARBON. 179 



Tlie Constitution of the Acid. — That the acid, C3H3N3O3, ^ IlgO, 

 obtained from formylchloridoxime by means of ammonia, is identical 

 with cyanisonitrosoacethydroxamic acid cannot at present be deter- 

 mined with certainty from its decomposition products. The consti- 

 tution of the acid as given is however extremely probable because of 

 its quantitative formation from sodic fulminate (two molecules) and 

 formylchloridoxime. 



The action of formylchloridoxime on sodic fulminate can, because 

 of the entirely analogous results obtained with phosgene on isocya- 

 nides,* take place only in the following manner. 



TT HON : CH C^N 



HON : Cp, + C . NONa = I = | + HoO. (I.) 



^^ Cl-C : NONa CIC : NONa 



Addition. 



C-=N 

 I 

 NaON:C-Cl-|-C:NONa 



CN 



I -t- H2O = CN-C : NONa 

 = NaON:C I -1- HCl. (H.) 



I HOC : NONa 



CIC : NONa 



Addition . Sodic-cyanisonitrosoacethydroxamate 



The reaction which takes place on treating formylchloridoxime with 

 ammonia is entirely analogous : a decomposition of the formylchlorid- 

 oxime into ammonium chloride and ammonic fulminate first takes 

 place as follows: 



^j^ C : NOH + 2 NH3 = C • NONH, + NH4CI. 



The ammonic fulminate thus formed (two molecules) then reacts with 

 unchanged formylchloridoxime (just as in the above equations does so- 

 dic fulminate) and ammonic cyanisonitrosoacethydroxamate is formed. 

 As can easily be seen, cyanisonitrosoacethydroxamic acid, 



CN-C: NOH 

 I 

 HOC : NOH, 



can readily go over by loss of water into a furazane derivative, 



CN-C = N\ 



I o, 



HOC = N/ 



* Ann. Chem. (Liebig), CCLXX. 286, 315. 



