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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
Author(s) -
Kolehmainen Erkki,
Laihia Katri,
Korvola Jorma,
Kauppinen Reijo,
Mänttäri Pia,
Rissanen Kari
Publication year - 1991
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260290313
Subject(s) - oxime , chemistry , nuclear magnetic resonance spectroscopy , carbon 13 nmr , organic chemistry , stereochemistry
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.