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Communication | Special issue | Vol 7, No. 2, 1977, pp.857-862
Published online, 1st January, 1970
DOI: 10.3987/S-1977-02-0857
The Beckmann Rearrangement of Bishomocubanone Oximes

Ken-ichi Hirao,* Hidetoshi Miura, and Osamu Yonemitsu

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

The Beckmann rearrangement of the title compounds gave brendane derivatives (7, 10, 17, 19, 22) through a regiospecific fission of the C2-C3 bond and hetero-cage lactams (8, 9) through a concerted rearrangement of intermediates (viii, ix). The product distribution depends on the reaction conditions.