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Paper | Regular issue | Vol 26, No. 7, 1987, pp.1891-1898
Published online, 1st January, 1970
DOI: 10.3987/R-1987-07-1891
■ Thermolysis of Sodium Salts of Tosylhydrazones of Some Heterocyclic Aldehydes in the Presence of Silver Chromate: 1,3 N→C Migration of Tosyl Group

Katsuhiro Saito and Hiraku Ishihara

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

Abstract

The thermal decompositions of sodium salts of tosylhydrazones of furfural. thiophene-2-aldehyde, 1-methylpyrrole-2-aldehyde, and pyridine-2-aldehyde in the presence of silver chromate gave 2-furyl(ptoluenesulfony1) methane. thiophene-2-(p-toluenesulfony1)methane, 1- methylpyrrole-2-(p-toluenesulfonyl)methane, and pyridine-2-(p-toluenesulfonyl) methane, respectively, via 1,3 N→C migration of tosyl group. The same type of reactions with sodium salts of tosylhydrazones of thiophene-3-aldehyde, pyridine-3-aldehyde, and pyridine-4-aldehyde also afforded the corresponding p-toluenesulfonylmethanes but the yields were slightly lower comparing to the above cases.