Imidoyl chlorides are organic compounds that contain the functional group RC(NR')Cl. A double bond exist between the R'N and the carbon centre. These compounds are analogues of acyl chloride. Imidoyl chlorides tend to be highly reactive and are more commonly found as intermediates in a wide variety of synthetic procedures. Such procedures include Gattermann aldehyde synthesis, Houben-Hoesch ketone synthesis, and the Beckmann rearrangement. Their chemistry is related to that of enamines and their tautomers when the α hydrogen is next to the C=N bond.[1] Many chlorinated N-heterocycles are formally imidoyl chlorides, e.g. 2-chloropyridine, 2, 4, and 6-chloropyrimidines.
^Ulrich, H. The Chemistry of Imidoyl Halides; Plenum Press: New York, 1968; pp. 55–112.
Imidoylchlorides are organic compounds that contain the functional group RC(NR')Cl. A double bond exist between the R'N and the carbon centre. These...
reaction. The imidoylchloride is the active chlorinating agent. Oxalyl chloride reacts with aromatic compounds in the presence of aluminium chloride to give...
Such reactions are believed to proceed via an imidoylchloride. In certain cases, the imidoylchloride is the final product. For example, pyridones and...
component of interest. This iminium species is a derivative of the imidoylchloride CH3N=CHCl. Analogues of this particular reagent are generated when...
acyl chlorides from carboxylic acids using oxalyl or thionyl chloride. The catalytic mechanism entails reversible formation of an imidoylchloride (also...
analogous process primary amides will react with thionyl chloride to form imidoylchlorides, with secondary amides also giving chloroiminium ions. These...
substrates relative to carboxylic acids. Further "activating" both acid chlorides (Schotten-Baumann reaction) and anhydrides (Lumière–Barbier method) react...
amination of nitriles. They are also generated by amination of an imidoylchloride. They are also prepared by the addition of organolithium reagents to...
isocyanides and acyl chlorides to form imidoylchloride products, a process first discovered by John Ulrich Nef. The product imidoylchloride can be hydrolyzed...
5-disubstituted and 1,4,5-trisubstituted imidazoles from aldimines and imidoylchlorides". Journal of Organic Chemistry. 42 (7): 1153–1159. Bibcode:1977JOrgC...
phosphabenzenes (phosphinines, or phosphorine) via functionalisation by imidoylchloride and insertion. Benzophosphole Metallole Organophosphorus compound Phosphorine...
photochemical ring opening of azirines and by dehydrochlorination of imidoylchlorides. The latter is the most reliable method. The synthetically most useful...
oxidising agent (e.g. NBS, or iodine); this potentially proceeds via an imidoyl halide. The method has been shown to be effective for a wide range of aromatic...
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