Isocyanide

Isonitriles (old name), or isocyanides (IUPAC -compliant name) are organic chemical compounds having the general structure RN ≡ C, where R is a carbon-containing radical such as an alkyl or aryl radical. The name is derived from the isomeric nitriles.

Production

Isonitriles arise from primary amines by reaction with chloroform and alkali. They are also formed in the reaction of silver cyanide with haloalkanes as byproducts of the Kolbe- nitrile. Isonitriles from the formamides primary amines are preferably prepared by dehydration with phosphorus oxychloride or p -toluenesulfonyl chloride.

Properties

Isonitriles are very malodorous, reactive and toxic substances. You are isosteric with carbon monoxide and therefore good complexing ligands. The hydrolysis of isonitriles yields formic acid and primary amines.

Use

Isonitriles are a Schlüsseledukt in numerous multi-component reactions, such as the Passerini reaction, the Ugi reaction and their variants.