Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Reactions of Sodium Salts of Tosylhydrazone Compounds with Silver Chromate. Formation of Indazole, Pyrazole, and Benzonitrile Derivatives
Katsuhiro SaitoTakashi TodaToshio Mukai
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1984 Volume 57 Issue 6 Pages 1567-1569


Tropone tosylhydrazone sodium salt was allowed to react with silver chromate to give 2-tosyl-2H-indazole. The reaction is thought to proceed through the cyclization of the hydrazyl radical intermediate. Under the same conditions, sodium salts of m-nitrobenzaldehyde tosylhydrazone (5), benzylideneacetone tosylhydrazone derivatives (7a and 7b), and β-ionone tosylhydrazone (9) reacted to yield m-nitrobenzonitrile from 5 and pyrazole derivatives from 7a, b, and 9, respectively. m-Nitrobenzonitrile is formed by homolytic fission of nitrogen–nitrogen bond of 5. Formation of the pyrazole derivatives can be explained by intramolecular 1,3-dipolar additions of the corresponding diazo intermediates.

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