Steric factors in the cyclization of 4-azaheptane-2,6-diones to dehydropiperid-3-ones and the stereochemistry of reduction of 2,2-dimethyl- and 5-neopentylpiperid-3-ones
Journal Article
·
· Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)
OSTI ID:6226045
The neopentyl substituent in the azadiketones of the type (Ib) completely blocks the cyclization to the dehydropiperidine systems with the participation of the acetonyl carbonyl as the electrophile. In such azadiketones, the geminal substitution at the carbon atom adjoining the nitrogen is less effective in its influence on the regioselectivity of the cyclization by comparison with the influence of substitution at the nitrogen. In the saturated 3-ketopiperidines, the axial substituent at C/sup 2/ largely blocks the e-coordinate of the approach of the hydride nucleophiles to the carbonyl or the e-adsorption in catalytic hydrogenation. The steric influence of the neopentyl substituent at C/sup 2/ on the carbonyl depends on the specificity of the particular reagent and can surpass the influence of the tert-butyl group.
- Research Organization:
- N.D Zelinskii Institute of Organic Chemistry, Moscow, USSR
- OSTI ID:
- 6226045
- Journal Information:
- Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 34:10; ISSN BACCA
- 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
ALKALI METALS
ALUMINIUM COMPOUNDS
AMINES
AZINES
BOROHYDRIDES
BORON COMPOUNDS
CARBONYLS
CATALYSTS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DEHYDROCYCLIZATION
ELEMENTS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROGENATION
INFRARED SPECTRA
KETONES
KINETICS
LITHIUM
METALS
MULTIPLETS
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PALLADIUM COMPOUNDS
PIPERIDINES
PLATINUM COMPOUNDS
PLATINUM OXIDES
PYRIDINES
REACTION KINETICS
REDUCTION
SODIUM COMPOUNDS
SPECTRA
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS
ULTRAVIOLET SPECTRA
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
ALKALI METALS
ALUMINIUM COMPOUNDS
AMINES
AZINES
BOROHYDRIDES
BORON COMPOUNDS
CARBONYLS
CATALYSTS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DEHYDROCYCLIZATION
ELEMENTS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROGENATION
INFRARED SPECTRA
KETONES
KINETICS
LITHIUM
METALS
MULTIPLETS
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PALLADIUM COMPOUNDS
PIPERIDINES
PLATINUM COMPOUNDS
PLATINUM OXIDES
PYRIDINES
REACTION KINETICS
REDUCTION
SODIUM COMPOUNDS
SPECTRA
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS
ULTRAVIOLET SPECTRA