Isocyanide dichloride


Isocyanide dichlorides are organic compounds containing the RN=CCl2 functional group. Classically they are obtained by chlorination of isocyanides. Phenylcarbylamine chloride is a well-characterized example.

Preparation

Chlorination of organic isothiocyanates is also well established:
Alkylisocyanates are chlorinated by phosphorus pentachloride:
Cyanogen chloride also chlorinates to give the isocyanide dichloride:

Reactions

Isocyanide dichlorides participate in Friedel-Crafts-like reactions, leading, after hydrolysis, to benzamides: