112 PROCEEDINGS OF THE AMERICAN ACADEMY 



On heating phenylisocyanide for six hours in a sealed tube at 

 130° with an alcoholic solution of sodium ethylate (1 molecule), 

 there is formed in large quantity diphenylformamidine * (mpt. 

 138°). The formation of this substance is explained most simply 

 by assuming that in the presence of sodium ethylate alcohol adds 

 itself to the phenylisocyanide, forming phenylformimidoether, 



/OC 2 H 5 



c 6 h 5 n=c; 



That such substances go over into diphenylformamidine, 



.NHCVEL; 

 C 6 H 5 N=C( 



with remarkable ease is evident from the work of Comstock and 

 Kleeberg; f and Pinner J also has shown how easily formimidoether, 



HN=c' 

 X H 



OC 2 H 5 



goes over into formamidine, 



HN=C 



NH 2 



X H 



Experiments undertaken with the object of adding sodium ethyl- 

 ate or methylate to phenyl- or o-tolylisocyanide have so far been 

 unsuccessful, because on heating in sealed tubes at 130°, much 

 polymerization takes place. Such an addition would be especially 



interesting, because carbonic oxide, 0=C^, according to Berthelot,§ 



directly adds caustic potash, 



OC= + KOH = OC^- K 



and, according to Geuther and Frohlich,|| also sodium methylate 



and ethylate, 



.ONa 

 OC= + NaOB = OCT 



X R 



* Hofmann, Jahresber. 1858, p. 854. 

 t Amer. Chem. Journal, XII. 498. 

 t Ber. d. chem. Ges., XVI. 354 and 1644. 

 § Ann. Chem. (Liebig), XCVII. 125. 

 || Ann. Chem. (Liebig), CCII. 290. 



