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imidoyl chloride
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.〔Ulrich, H. The Chemistry of Imidoyl Halides; Plenum Press: New York, 1968; pp. 55–112.〕
== Synthesis and properties==
Imidoyl halides are synthesized by combining amides and halogenating agents. The structure of the carboxylic acid amides plays a role in the outcome of the synthesis.Imidoyl chloride can be prepared by treating a monosubstituted carboxylic acid amide with carbonyl chloride.〔
:RC(O)NHR’ + COCl2 → RC(NR’)Cl + HCl + CO2
Imidoyl chlorides are generally colorless liquids or low-melting solids that are sensitive to both heat and especially moisture. In their IR spectra these compounds exhibit a characteristic νC=N band near 1650–1689 cm−1. Although both the syn and anti configurations are possible, most imidoyl chlorides adopt the anti configuration.〔
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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