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Study of Hydrazone-Hydrazoimine Tautomerism in  α-Azo-6-ketomethylphenanthridines

H. Loghmani-Khouzani^a,*, H. Mehrabi^a, M.M.M. Sadeghi^a and R. Gawinecki^b

^aDepartment of Chemistry, Faculty of Sciences, University of Isfahan, 81746-73441 IR, Iran
^bDepartment of Chemistry, Technical and Agricultural University, Seminaryjna 3PL 85-326 Bydgoszcz, Poland

AB Azo-coupling of a series of 6-ketomethylphenanthridines products was performed starting from 6-ketomethylphenanthridines and benzene diazonium chloride. The products were characterised using ¹H, ¹³C and ¹⁵N NMR, IR, UV and MS spectroscopic methods. The hydrazoimine forms were the only tautomer present in chloroform solution. Two rotamers were detected in chloroform solutions of the compounds studied. Analysis of the NMR data shows that the ratio of rotamers depends on electron-donating and electron-withdrawing properties of the substituent present in the benzene ring.

Keywords: Tautomerism, Hydrazone, Hydrazoimine, Azo-coupling, α-Azo-6-ketomethylphenanthridines