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Isocyanide dichloride

Isocyanide dichlorides are organic compounds containing the RN=CCl<sub>2</sub> 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:

RN=C=S + 2Cl<sub>2</sub> → RN=CCl<sub>2</sub> + SCl<sub>2</sub>

Alkylisocyanates are chlorinated by phosphorus pentachloride:

RN=C=O + PCl<sub>5</sub> → RN=CCl<sub>2</sub> + POCl<sub>3</sub>

Cyanogen chloride also chlorinates to give the isocyanide dichloride:

ClCN + Cl<sub>2</sub> → ClN=CCl<sub>2</sub>

Reactions

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

RN=CCl<sub>2</sub> + ArH → RN=C(Cl)Ar + HCl
RN=C(Cl)Ar + H<sub>2</sub>O → R(H)NC(O)Ar + HCl

References