Beckmann rearrangement and reduction of the E isomer of 1,5,5-trimethylbicyclo(2. 2. 1)heptan-2-one oxime
Journal Article
·
· J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:7199945
In the Beckmann rearrangement of the E isomer of 1,5,5-trimethylbicyclo(2.2.1)-heptan-2-one (isofenchone)oxime 1,6,6-trimethyl-2-azabicyclo(3.2.1)octan-3-one was obtained as a result of stereospecific migration of the C/sup 2/ carbon atom situated in the anti position to the hydroxime hydroxyl group. Reduction of the product with lithium aluminum hydride led to 1,6,6-trimethyl-2-azabicyclo(3.2.1)-octane. Reduction of isofenchone oxime with lithium aluminum hydride in THF leads to the formation of a mixture of 1,5,5-trimethylbicyclo(2.2.1)hept-2-yl-endo-amine, the corresponding exo-amine, and 1,6,6-trimethyl-2-aza- and 1,6,6-trimethyl-3-azabicyclo(3.2.1)octanes in ratios of 45:10:5:40. The /sup 1/H and /sup 13/C NMR spectra were measured on a Bruker WM-360 spectrometer at 360 MHz for /sup 1/H and 90 MHz for /sup 13/C. The compounds were prepared for the spectra in the form of 10% solutions in deuterochloroform.
- Research Organization:
- Institute of Physical Organic Chemistry, Minsk (USSR)
- OSTI ID:
- 7199945
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:5; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
ALKANES
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
AMINES
CARBON 13
CARBON ISOTOPES
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CYCLOALKANES
DEUTERIUM COMPOUNDS
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HYDRIDES
HYDROCARBONS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INFRARED SPECTRA
ISOMERIZATION
ISOMERS
ISOTOPES
KETONES
LIGHT NUCLEI
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
MULTIPLETS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIMES
REDUCTION
SPECTRA
STABLE ISOTOPES
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
ALKANES
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
AMINES
CARBON 13
CARBON ISOTOPES
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
CYCLOALKANES
DEUTERIUM COMPOUNDS
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HYDRIDES
HYDROCARBONS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INFRARED SPECTRA
ISOMERIZATION
ISOMERS
ISOTOPES
KETONES
LIGHT NUCLEI
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
MULTIPLETS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIMES
REDUCTION
SPECTRA
STABLE ISOTOPES