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Paper | Regular issue | Vol 53, No. 5, 2000, pp.1121-1128
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8879
An Unprecedented 1,8a-Bond Fission of an N -Formyl-1,2,3,4-tetrahydroisoquinoline Derivative under a Nitration Condition

Toshio Honda,* Masato Nishimura, Jun Itabashi, and Kazuo Kanai

*Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan


An unprecedented bond fission between the 1 and 8a positions of an N-formyl-1,2,3,4-tetrahydroisoquinoline derivative was observed under nitration conditions using nitric acid and acetic acid. The structures of the products and the proposed reaction mechanism were also described.