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Paper | Regular issue | Vol 36, No. 9, 1993, pp.1997-2004
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6328
Reactions of Tosylhydrazones of 2-Methoxy-1-azaazulene-3-carboxaldehyde and Azulene-1-carboxaldehyde with Styrenes and Stilbenes

Katsuhiro Saito,* Hiroshi Fushihara, Kiichiro Tominaga, Kyoko Kumagai, Satoru Kondo, Kunihide Fujimori, Noritaka Abe, and Kensuke Takahashi

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


The reactions of sodium salt of 2-methoxy-1-azaazulene-3-carboxaldehyde tosylhydrazone with styrenes gave 3,8-cyclohexeno-2-methoxy-1-azaazulenes and 3-cyclopropyl-2-methoxy-1-azaazulenes. The formers were afforded through the diazo compound generated from the tosylhydrazone and the latters were yielded via the carbene derived from the diazo compound. The reactions with stilbenes gave the corresponding cyclopropane derivatives. The similar reactions with sodium salt of azulene-1-carboxaldehyde tosylhydrazone gave the analogous result.