Halogenation of Amines, Imines and Carbamoyl Chlorides

The chlorination of certain cyclic amines and carbamoyl chlorides affords imidoyl chlorides ( ) however, this method is of only limited synthetic value. 

For example, high-temperature chlorination of the morpholine derivative (LXXVI) affords the heterocyclic imidoyl chloride (LXXVII) 

Likewise, the heterocyclic bis-imidoyl chloride (LXXVIII) has been obtained in the high-temperature chlorination of the quinone derivative LXXIX( ). 

The chlorination of N-ethyl benzaldimine (LXXX) gives rise to the formation of the imidoyl chloride LXXXI 

The reaction of trichlorovinylamines, such as LXXXII, which are obtained from N,N-disubstituted 2.2,2-trichloroacetamides and tertiary phosphines, with hydrogen chloride affords the iminium salts LXXXIII 

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