Tetrahedron p. 3405 - 3412 (1988)
Update date:2022-08-04
Topics:
Hill, Richard K.
McKinnie, B. Gary
Conley, Robert T.
Darby, Paul S.
Halbeek, Herman van
Holt, Elizabeth M.
Heating camphor oxime with PPA affords, besides the known fragmentation products isoaminocamphor (4) and β-campholenonitrile (13), four isomeric ketones C10H14O resulting from intramolecular acylation of the intermediate α-campholenonitrile (3).The ketones have been identified as 5-ketocamphene (6), 6-ketocamphene (8), tricyclenone (9), and endo-2,4-dimethylbicyclo<3.2.1>oct-2-ene-7-one (14).The latter results from a novel ring expansion, probably by way of a protonated cyclopropane.
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