OP ARTS AND SCIENCES. 113 



Gautier * noticed that niethylisocyanide reacts with methyl- 

 iodide, and forms, hesides much resinous matter, a product soluble 

 in water. That in this case no addition product, 



/I 

 CH,N=CT 



X CH 3 



has been formed, but that polymerization has taken place, follows 

 from the work of Ljubjawin,f who studied this reaction more 

 closely. It follows further from the investigations of Wallach, t 

 that a substance of the above nature must be very unstable, if in- 

 deed capable of existence ; and that it would probably lose hydrio- 

 dic acid and go over into basic products. I found, as did Ljubjawin 

 in the case of ethylisocyanide, that on heating phenylisocyanide 

 with ethyliodide at 100° exclusively polymerization takes place. 

 That phenylisocyanide reacts with hydrogen sulphide, forming 



thioformanilide, 



.SH 

 C 6 H 5 N<T 



X H 



has been shown by Hofmann § ; that it reacts with sulphur to form 

 phenylmustard oil, C 6 H 5 N=OS, has been made probable by the 

 experiments of Weith,|| who obtained sulphocarbanilide on heating 

 phenylisocyanide containing aniline with sulphur. Weith H has 

 also shown that on heating aniline and phenylisocyanide in sealed 

 tubes at 220°, diphenylformamidine 



NHC 6 H 5 

 C 6 H 6 N=c' 



X H 



is formed. I can confirm his experiments, and obtained 30% yield 

 in this case. 



On pouring phenylisocyanide over dry silver oxide, or mercuric 

 oxide, an extremely energetic reaction takes place : an ethereal 

 solution of the isonitrile, with one molecule of mercuric oxide, 

 heated to about 60° in a sealed tube, exploded with great violence. 

 On heating the same mixture gently on a water bath with reversed 



* Loc. cit, XVII. 226. 



t Ber. d. chem. Ges., XVIII. R. 407. 



\ Ann. Chem. (Liebig), CLXXXIV. 86 and 108, CCXIV. 221. 



§ Ber. d. chem Ges., X. 1095. 



|| Ibid., VI. 210. f Ibid., IX. 454. 



VOL. XXVII. (n. S. XIX.) 8 



