NEF. — BIVALENT CARBON. 151 



VI. 



CONTRIBUTIONS FROxM THE KENT CHEMICAL LABORATORY 

 OF THE UNIVERSITY OF CHICAGO 



ON BIVALENT CARBON. 



SECOND PAPER* 

 By J. U. Nef. 



Presented May 9, 1894. 



The bivalent carbon atom in methyl- and in ethyl-isocyanide shows 

 itself much more reactive, as was to be expected, than in the case of 

 the aromatic isocyanides. The reactions, however, are otherwise 

 entirely analogous to those obtained in the case of the aromatic com- 

 pounds, as is evident from the following experiments. 



I. On Ethyl and Methyl Isocyanide. 



CeHsCO— COH 



Benzoylformic Methylamide^ II 



NCHg. 



The methylisocyanide used was made according to the method of 

 Gautier,t by heating 100 grams silver cyanide and 100 grams methyl- 

 iodide for two hours on a water bath (with reversed condenser and with 

 a mercury valve). This substance unites with benzoylchloride slowly 

 already at ordinary temperatures, as is recognized by the yellow color- 

 ation which sets in. 10.2 c.cm. methylisocyanide and 27 grams ben- 

 zoylchloride (one molecule) are mixed and heated for half an hour at 

 100° in a sealed tube. No more isonitrile is left, and longer heating 

 is harmful, since much formation of resin (polymerization) then takes 

 place. The crude product is taken up with absolute ether, filtered off 

 from brown resinous flakes, and the residual oil, after getting rid of 

 the ether, treated with water, whereby on standing, or rubbing with 



* First Paper, tliese Proceerlings, XXVII. 102-162. 

 t Annales de Chim. et de Phys., [4.], XVII. 216. 



