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Synthesis 1987; 1987(12): 1097-1098
DOI: 10.1055/s-1987-28181
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A Convenient Synthesis of 7-Nitrobicyclo[2.2.1]heptane from Bicyclo[2.2.1]hept-2-ene via 7-Aminobicyclo[2.2.1]heptane

Kimitoshi Fukunaga* , Christoph Rüchardt
  • *Faculty of Engineering of Yamaguchi University, Tokiwadai, Ube, 755 Japan
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Publication Date:
20 August 2002 (online)

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syn-7-(Methoxycarbonylamino)bicyclo[2.2.1]hept-2-ene (5), prepared from bicyclo[2.2.1]hept-2-ene (1) in 52% overall yield according to literature procedures, was hydrogenated over palladized charcoal to yield 7-(methoxycarbonylamino)bicyclo[2.2.1]heptane (6). Alkaline hydrolysis of 6 gave 7-aminobicyclo[2.2.1]heptane (7), which was readily oxidized with m-chloroperoxybenzoic acid in boiling dichloroethane to 7-nitrobicyclo[2.2.1]heptane (8). The reported synthesis constitutes an efficient entry into the 7-substituted bicyclo[2.2.1]heptane series and allows for the preparation of the previously unknown nitro-derivative 8 in 23% overall yield from 1.