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Report | Regular issue | Vol 24, No. 5, 1986, pp.1291-1294
Published online, 1st January, 1970
DOI: 10.3987/R-1986-05-1291
Termolysis of Sodium Salt of Furfural Tosylhydrazone in the Presence of Silver Chromate: Formation of 2-Furyl(p-toluenesulfonyl)methane via 1,3-NC Migration of Tosyl Group

Katsuhiro Saito* and Hiraku Ishihara

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


The thermal decomposition of sodium salt of furfural tosylhydrazone in diglyme in the presence of silver chromate afforded trans-1,2-di(2-furyl)ethylene and 2-furyl(p-toluenesulfonyl)methane. The former product is formed via (2-furyl)methylene, while the latter product is considered to be derived via 1,3 N→C migration of tosyl group in furfural tosylhydrazyl radical, which is generated by one electron oxidation of furfural tosylhydrazone by silver chromate.