NEF. — BIVALENT CARBON. 1<J1 



ordinary temperature, after a time most tremendous explosions take 

 place ; these can be entirely avoided as follows. 28.7 grams silver ful- 

 minate, 50 grams ethyliodide, and 38 grams absolute ether are brought 

 into a flask, which is constantly kept m cold water, and allowed to 

 stand thus for three weeks, takuig care to shake well from time to time. 

 At first, in the course of the reaction, a very strong smell of ethylcya- 

 nate is noticed (Calmels says smell of chlorpicrin) and towards the 

 end a smell resembling that of ethylisocyanide is noticed. 



The investigation of the products formed has shown that they con- 

 sist chiefly of ethylcyanate and its polymer ethylcyanurate, whereas very 

 little of the substance smelling like ethylisocyanide is formed. It 

 seems to me, however, extremely probable that this product is not 

 ethylisocyanide, but ethylcarbyloxim, C : NOCgHg, the formation of 

 Avhich from silver fulminate, C; NOAg, and ethyliodide is self-evident. 

 The formation of ethylcyanate, or of its polymer, which is the chief 

 product of the above reaction, is easily explained by an addition of 

 ethyliodide to the unsaturated carbon atom present in silver fulminate, 



AgON : C 4- IC2H5 = AgON : cj. „ 



The addition product is then converted by Beckmann's rearrange- 

 ment into ethylcyanate and silver iodide. 



TT 



Formation of Ethoxyformamidine, C2H5ON : C^rx 



26 grams isuretine w^ere heated, in alcoholic solution, with one 

 molecule of sodium ethylate and ethyliodide (1^ molecules), for three 

 hours with reversed condenser; the alcohol was thereupon distilled 

 off, and a strong smell of isonitrile and ammonia was noticed. The 

 residue was dissolved in water and repeatedly extracted with ether. 

 After distilling off the ether, and fractionating the liquid remaining, 

 3 grams of an ethereal weak basic smelling oil were obtained, which 

 boils without decomposition at 170°-175°. Up to the present only 

 7 grams of this oil have been obtained, which, in view of an analysis 

 of a platinum double salt obtained from it, must be regarded as ethoxy- 

 formamidine. It is easily soluble in water; a portion was dissolved in 

 hydrochloric acid, and the evaporated solution takeo up in alcohol 

 and treated with platinic chloride. On addition of ether a yellow oil 

 separates out, which, on rubbing with a glass rod, solidifies. The 

 salt was recrystallized from alcohol and ether, and obtained in yellow 

 quadratic plates, melting at 153° 



