REACTIONS OF SODIUM SALTS OF TOSYLHYDRAZONE COMPOUNDS WITH SILVER CHROMATE. FORMATION OF INDAZOLE, PYRAZOLE, AND BENZONITRILE DERIVATIVES.

Article abstract of DOI:10.1246/bcsj.57.1567

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 beta -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.