Goldschmidt, Ber., 1886, 19, p. 3232); by the action of dilute hydrochloric acid on the isonitriles, Rï¿½NC+2H20=Rï¿½NH2-}-H2C02; by heating the mustard oils with a mineral acid, by the hydrolysis of the alkyl phthalimides (S.
Primary amines when heated with alcoholic potash and chloroform yield isonitriles, which are readily detected by their offensive smell.
- Hydrocyanic acid forms two series of derivatives by the exchange of its hydrogen atom for alkyl or aryl groups; namely the nitriles, of type R CN, and the isonitriles, of type R NC. The latter compounds may be considered as derivatives of the as yet unknown isohydrocyanic acid HNC.
The Isonitriles (isocyanides or carbylamines) were first prepared in 1866 by A.
The carbon atom in the isonitriles is assumed by J.
Soc., 1902, 81, p. 1 59 6) who showed that the products obtained by the action of alkyl iodides on the isonitriles in alcoholic solution at 100° C. yield amine hydroidides and formic acid when hydrolysed.
At 200° C. the isonitriles are converted into nitriles.
- Considerable discussion has taken place as to the structure of the metallic cyanides, since potassium cyanide and silver cyanide react with alkyl iodides to form nitriles and isonitriles respectively, thus apparently pointing to the fact that these two compounds possess the formulae KCN and AgNC. The metallic cyanides are analogous to the alkyl isocyanides, since they form soluble double silver salts, and the fact that ethyl ferrocyanide on distillation yields ethyl isocyanide also points to their isocyanide structure.
Wade (loc. cit.) explains the formation of nitriles from potassium cyanide, and of isonitriles from silver cyanide by the assumption that unstable addition products are formed, the nature of which depends on the relative state of unsaturation of the carbon and nitrogen atoms under the varying conditions: KNC--KN :C(:C 2 H 5 I) --SKI +C2H5CN, AgNC->AgN(:C2H51)C---AgI-f-C2H5NC; that is, when the metal is highly electro-positive the carbon atom is the more unsaturated, the addition takes place on the carbon atom, and nitriles are produced.
Isonitriles are produced.