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Communication | Regular issue | Vol 3, No. 6, 1975, pp.445-448
Published online, 1st January, 1970
DOI: 10.3987/R-1975-06-0445
A Radical Reaction of Tropone Tosylhydrazone Leading to 2-Tosylindazole

Katsuhiro Saito,* Takashi Toda, and Toshio Mukai

*Faculty of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Silver chromate oxidation of tropone tosylhydrazone sodium salt (I) afforded 2-tosylindazole (II). The reaction is considered to proceed via an hydrazyl radical intermediate (III). Under the same reaction conditions m-nitrobenzaldehyde tosylhydrazone sodium salt provided m-nitrobenzonitrile probably via m-nitrobenzylideneaminyl radical.