NEF. — BIVALENT CARBON. 161 



Notwithstanding this, all the formula) yet proposed for fulminic 

 acid, as, fur example, that of 



C : NOH HOC = N\ HC = N-0 



Steiner,* II of Divers, f I O, of Scholl,| I ) 



C:NOH, HC = N/ HC = N-0, 



and many others, have originated from the assumption that this sub- 

 stance contains two carbon atoms in the molecule, because it was 

 regarded as proved by the experiments of Liebig and Gay-Lussac § 

 that the fulminic acid molecule contains two hydrogen atoms possess- 

 ing entirely different functions. The behavior of mercury fulmi- 

 nate towards bromine || and towards iodine,1[ whereby products are 

 formed which unquestionably contain two carbon atoms in the mole- 

 cule, as well as the decomposition of this salt, by means of chlorine, 

 into cyanogen chloride and chlorpicrine,** seem also to be in favor of 

 this conclusion. Only very recently has Scholl ft thought of the 

 possibility of the simple carbyloxime formula, C : NOH, but he still 

 gives the polymerized formula of Steiner, 



C:NOH /C\ 



II , or HON II NOH, the preference. ^ 



C : NOH \ C / 



I have succeeded in proving experimentally, with absolute precision, 

 that fulminic acid is identical with carbyloxime, C : NOH, and that 

 the bivalent carbon atom present in this substance possesses a most 

 surprising and enormous reactivity, so that in all reactions shown by 

 fulminic acid salts the unsaturated carbon atom is the point of attack ; 

 and, since we now possess some light on the nature of bivalent carbon, 

 the entire chemistry of the fulminic acid derivatives is very simply 

 and completely explained, as will become evident from the following 

 experiments. 



It has for over seventy years been considered as settled that, on 

 treating fulminic acid salts with dilute hydrochloric acid, a complete 

 destruction of the fulminic acid molecule takes place, and that among 



* Ber. d. chem. Ges., XVI. 1484, 2419. 



t Journ. cliem. Soc, XLV. 21. 



t Ber. de chem. Ges., XXIII. 3497, 3507. 



§ Annales de Chim. et de Phys., XXIV. 294-317, XXV. 285-310. 



II Kekule, Ann. Chem. (Liebig), CV. 280. 



IT Sell and Biedermann, Ber. d. chem. Ges , V 89. 

 ** Kekule', Ann. Chem. (Liebig), CI. 206 

 tt Ber. d. chem. Ges., XXIII. 350fi-3509. 

 tt Ber. d. chem. Ges., XXIV. 581. 



VOL. XXX. (N. 8. XXII.) 11 



