NOVEL PRODUCTS FROM BECKMANN FRAGMENTATION OF CAMPHOR OXIME IN POLYPHOSPHORIC ACID

Article abstract of DOI:10.1016/S0040-4020(01)85976-7

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.