138 PROCEEDINGS OP THE AMERICAN ACADEMY 



and, to a slight degree, as I have found, of formanilide, 



.OH 



c 6 h 5 n=c; 



X H 



on distillation. In these two cases, however, notwithstanding 

 many experiments, it was found impossible to attain a quantitative 

 splitting off of H 2 S or H 2 respectively, because at higher tem- 

 perature the isonitriles polymerize to a marked extent. 



A decomposition in the same direction has also been observed by 

 TVallach,* on distilling 



OH 



c 2 h 5 n<t 



x C0 2 C 2 H 5 

 and by Klinger, f on distilling oxanilethane, 



OH 



c 6 h 5 x=c; 



x C0 2 C 2 H 5 



The formation of isonitriles and their polymeric products (resins) 

 in the above cases shows how strong a tendency exists for the split- 

 ting off in this direction. This same thing is to be seen in the 

 decompositions described above under pyruvic-anilidimidechloride 

 (pp. 127 and 128). 



II. Ox o-ToLTLisocvANiDE, CH 3 -C 6 H 4 N=C=. 



Prejiciration of o-Tolyllsocyanide. — 210 grams of caustic potash 

 are dissolved in about 800 c.c. alcohol (99%), and a mixture of 

 190 grams chloroform and 100 grams o-toluidine added slowly, 

 following in other respects the directions given under phenyliso- 

 cyanide. 



Whereas, in the case of aniline only about 15 grams pure phenyl- 

 isocyanide are obtained from 100 grams of the amine taken, here 

 at least 25 grains pure o-tolylisocyanide always result. 



o-Tolylisocyanide boils constant and without leaving any residue 

 at 75° at 16 mm., and at 101° at 55 mm. pressure: it boils with but 

 slight decomposition at 183°-184° (thermometer entirely in the 

 vapor) at ordinary pressure (753 mm.). It is a colorless oil, its 

 specific gravity being 0.968 at 24° (Westphal) : on standing, the 



* Ann. Chem. (Liebig), CLXXXIV. 60. 

 t Ann. Chem. (Liebig), CLXXXIV. 265. 



