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Paper | Regular issue | Vol 31, No. 8, 1990, pp.1491-1496
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5428
Reaction of Azepines with Palladium (II) Acetate: Formation of Mucondialdehyde and Dihydroazepine Derivative

Katsuhiro Saito,* Masatoshi Kozaki, and Kensuke Takahashi

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

Abstract

Reaction of 1-carboethoxy-1H-azepine with palladium (II) acetate in chloroform or acetonitrile afforded trans-trans-mucodialdehyde together with ethyl carbamate. On the other hand, the analogous reaction in acetic acid gave 1-carboethoxy-2,3-diacetoxy-2,3-dihydro-1H-azepine. The same reaction but using 1-carboethoxy-1H-1,2-diazepine gave a nitrile derivative via a ring opening.