Multinuclear Magnetic Resonance Study of 1,3,3-Trimethylbicycloheptan-2-one (Fenchone) Oxime, Its Five Monochloro Derivatives and a Dehydrochlorination Product

Article abstract of DOI:10.1002/mrc.1260290313

Fenchone oxime, 5-exo-chlorofenchone oxime, 6-exo-chlorofenchone oxime, 7-anti-chlorofenchone oxime, 8-chlorofenchone oxime, 9-chlorofenchone oxime and a dehydrochlorination product of 10-chlorofenchone oxime were synthesized from fenchone and the corresponding chlorofenchones.The 1H, 13C and 17O NMR spectra of the oximes and the dehydrochlorination product were recorded.The NMR data were compared with the corresponding parameters obtained earlier for fenchone and monochlorofenchones in order to determine the differences between the carbonyl and oxime substituents from the NMR spectroscopic point of view, and to assign the stereochemistry of the oxime group.The stereochemistry could not, however, be assigned solely by NMR spectroscopy.