Potassium Tellurocyanate Mediated Coupling Reactions of N -(1-Chloroethylidene)Arylamines.

The reaction of potassium tellurocyanate (prepared in situ) withN-(1-chloroethylidene)arylamines (i.e., 4-RC6H4N = C(CH3)Cl, where R = H, Cl, CH3and NO2) in DMSO solution gave unexpectedly, after hydrolysis, the correspondingN-(3-(arylamino)butan-2-ylidene)arylamines in 63–78%. Reaction ofN-(3-(arylamino)butan-2-ylidene)arylamines with SOCl2or with Br2resulted in the substitution of a halogen on the aromatic rings. The presence of a water molecule within the structure of the synthesized diimines was rationalized theoretically by Density Functional Theory (DFT). All compounds were characterized by elemental analysis, IR, NMR and mass spectroscopic data. [ABSTRACT FROM AUTHOR]