Isocyanide

Encyclopedia : I : IS : ISO : Isocyanide

An isocyanide (erroneously called isonitrile) is a functional group in organic synthesis containing carbon and nitrogen. The functional group is connected to the main body via the nitrogen atom (opposite to a cyanide and hence the prefix iso). Nitrogen and carbon are connected through a triple bond with a positive charge on nitrogen and a negative charge on carbon.

The first isocyanide, allyl isocyanide was prepared in 1859 by the chemist Lieke from allyl iodide and silver cyanide. Commonly they are synthesized by the reaction of primary amines with dichlorocarbene or by dehydration of a formamide with phosphorus oxychloride.

Isocyanides are isoelectronic with CO yet are only moderately toxic. Their disagreeable odour is legendary. Tosylmethyl isocyanide (TOSMIC) is a notable exception.

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