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Paper | Regular issue | Vol 48, No. 6, 1998, pp.1151-1156
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8103
Electrochemistry of 7-Carboethoxycycloheptatriene and Its Aza-analogues: Ring Contruction of Azepine Derivatives to AnilineDerivatives by Oxidation and N—N Bond Rupture of Diazepine Derivatives to 1-Amino-4-cyano-1,3-butadiene Derivatives by Reduction

Satoru Kondo, Hiroshi Suzuki, Tatsuya Hattori, Takayasu Ido, and Katsuhiro Saito*

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


Electrochemical reduction or oxidation of 7-ethoxycarbonylcycloheptariene afforded 2-ethoxycarbonylcycloheptatriene and ethyl phenylacetate, respectively. N-Alkoxycarbonyl-1H-azepine formed N-alkoxycabonylaniline in electrochemcial oxidation via a ring contruction. N-Alkoxycarbonyl-1H-1,2-diazepine afforded N-alkoxycarbonyl-1-amino-4-cyano-1,3-butadiene in electrochemical reduction via an N-N bond fission.