Study of hydrazone-Hydrazoimine tautomerism in α-Azo-6-ketomethylphenanthridines

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 1 H, 13 C and 15 N NMR, IR, UV and MS spectroscopic methods. The hydrazoimine forms were the only tautome...

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Bibliographic Details
Published inJournal of the Iranian Chemical Society Vol. 6; no. 1; pp. 129 - 137
Main Authors Loghmani-Khouzani, H., Mehrabi, H., Sadeghi, M. M. M., Gawinecki, R.
Format Journal Article
LanguageEnglish
Published Berlin/Heidelberg Springer-Verlag 01.03.2009
Subjects
Analytical Chemistry
Biochemistry
Chemistry
Chemistry and Materials Science
Inorganic Chemistry
Organic Chemistry
Physical Chemistry
Hydrazoimine
Tautomerism
Hydrazone
α-Azo-6-ketomethylphenanthridines
Azo-coupling
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Summary: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 1 H, 13 C and 15 N 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.
ISSN:1735-207X
1735-2428
DOI:10.1007/BF03246511