Multinuclear magnetic resonance study of 1,3,3-trimethylbicyclo [2.2.1]heptan-2-one (fenchone) oxime, its five monochloro derivatives and a dehydrochlorination product

✍ Scribed by Erkki Kolehmainen; Katri Laihia; Jorma Korvola; Reijo Kauppinen; Pia Mänttäri; Kari Rissanen

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 513 KB
• Volume: 29
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260290313

✦ Synopsis

Abstract

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 ^1^H, ^13^C and ^17^O 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. This stereochemistry could not, however, be assigned solely by NMR spectroscopy.