OP ARTS AND SCIENCES. 107 



and hydrobromic acid. We know now, because of the experiments 

 of Michael and Wing,* that the resulting compounds are not salts, 

 hut addition products : acetonitrile, for example, forms with hydro- 

 chloric acid 



CH3-ONH 

 \ 

 CI 



It is now pretty generally conceded, especially also because of 

 Wallach's f experiments, that hydrochloric acid forms with alkyl- 

 cyanides either amide or imidechlorides, 



^NH 2 /NH 



R-(T or R-Cf 



X C1 2 X C1 



Gautier t has brought forward as a further proof for his carbyl- 

 amine formula the fact that methyl and ethyl cyanate are formed by 

 the oxidation of methyl and ethyl isocyanide respectively. These 

 oxidation products, however, are formed as side products, the chief 

 products being very complicated compounds, as C 7 H 12 lSr 2 04 and 

 C 8 H 12 N 4 5 (from CH 3 NC), and C 9 H 22 N 4 O a as well as C l3 H 25 N" 5 4 

 (from C 2 H 5 NC). 



It seems to me, therefore, that this reaction cannot be regarded 

 as sufficient to decide the constitution of the isonitriles, since it is 

 likely that a substance having the constitution RN V =C IV may also 

 give alkylcyanate, R]ST = C = 0, by oxidation. 



The chief argument of Gautier for his carbylamine formula, 



p„ -] N m , namely, the supposed strong basic properties of the com- 

 pounds, has already been proved untenable. Furthermore, the pres- 

 ent views with regard to the nature of the isonitriles differ; whereas 

 some chemists § consider the presence of bivalent carbon as possi- 

 ble; others, as Hofmann,|| V. Meyer and Jacobson,1[ v. Richter,** 

 favor the formula R-^C, while Beilstein ff simply writes RNC. 

 The above briefly stated facts, which are given in detail in the 



* Amer. Chera. Journal, VII. 72. 



t Ann. Chem. (Liebig), CLXXXIV. 1, CCXIV. 192 



t Loc. at., XVII. 228, 242, 255. 



§ Graham Otto, Lehrbuch der org. Chemie, neue Ausgabe von Kolbe und 

 E. v. Meyer. 



|| Ber. d. chera. Ges., X. 1095. 

 IT Lehrbuch der org. Chemie, I. 252. 

 ** Ibid., translation by E. F. Smith, p. 287. 

 tt Handbuch der org. Chemie, I. 1173, Zweite Aufl. 



