Isocyanide dichloride

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An 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 and reactions

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Chlorination of organic isothiocyanates is also well established:[1]

RN=C=S + 2 Cl2 → RN=CCl2 + SCl2

Alkylisocyanates are chlorinated by phosphorus pentachloride:

RN=C=O + PCl5 → RN=CCl2 + POCl3

Cyanogen chloride also chlorinates to give the isocyanide dichloride:[1]

ClCN + Cl2 → ClN=CCl2

Reactions

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

RN=CCl2 + ArH → RN=C(Cl)Ar + HCl
RN=C(Cl)Ar + H2O → R(H)NC(O)Ar + HCl

References

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  1. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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