Isocyanide dichlorides are

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

s containing the RN=CCl₂

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

. Classically they are obtained by chlorination of

isocyanide An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group –. It is the isomer of the related nitrile (–C≡N), hence the prefix is ''isocyano''.IUPAC Goldboo''isocyanides''/ref> The organic fragme ...

s. Phenylcarbylamine chloride is a well-characterized example.

Preparation and reactions

Chlorination of organic isothiocyanates is also well established: :RN=C=S + 2{{nbspCl₂ → RN=CCl₂ + SCl₂ Alkylisocyanates are chlorinated by

phosphorus pentachloride Phosphorus pentachloride is the chemical compound with the formula . It is one of the most important phosphorus chlorides/oxychlorides, others being and . finds use as a chlorinating reagent. It is a colourless, water-sensitive solid, althoug ...

: :RN=C=O + PCl₅ → RN=CCl₂ + POCl₃

Cyanogen chloride Cyanogen chloride is an inorganic compound with the formula . This triatomic pseudohalogen is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compound cyanogen bromide, a room-temperature solid that is ...

also chlorinates to give the isocyanide dichloride: :ClCN + Cl₂ → ClN=CCl₂

Reactions

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

benzamide Benzamide is an organic compound with the chemical formula of C7H7NO. It is the simplest amide derivative of benzoic acid. In powdered form, it appears as a white solid, while in crystalline form, it appears as colourless crystals. It is slightly ...

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

References

Functional groups Isocyanides Organochlorides