Nucleophilic addition of nitriles to secondary terpene alcohols
Journal Article
·
· J. Gen. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:5355031
The addition of nitriles of varying nucleophilicity to isocamphanol and exo-1,5,5-trimethyl-bicyclo(2.2.1)heptan-2-ol (isofenchol) was investigated. The authors examined the effect of the reaction conditions on the yield and structure of the target products of the reaction: N-substituted amides. As a result of the study, it was shown that in the reaction with chloroacetonitrile, propionitrile, methoxypropionitrile, isovaleronitrile, and phenylacetonitrile under the conditions of the Ritter reaction, isocamphanol is transformed into the corresponding substituted exo-N-acyl-1,7,7-trimethylbicyclo(2.2.1)hept-2-ylamines, as in the reaction with aceto- and benzonitriles, due to 2,6-hydride displacement accompanied by Wagner-Meerwein rearrangement. The structures of these amides were demonstrated by PMR spectroscopy.
- Research Organization:
- Institute of Physical and Organic Chemistry, Minsk (USSR)
- OSTI ID:
- 5355031
- Journal Information:
- J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 56:7; ISSN JGCHA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALCOHOLS
ALKANES
AMIDES
AMINES
CARBON 13
CARBON ISOTOPES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
CYCLOALKANES
DEUTERIUM COMPOUNDS
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HEPTANE
HYDROCARBONS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
HYPERFINE STRUCTURE
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
METHANOL
MOLECULAR STRUCTURE
MULTIPLETS
NITRILES
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SPECTRA
STABLE ISOTOPES
TERPENES
YIELDS
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALCOHOLS
ALKANES
AMIDES
AMINES
CARBON 13
CARBON ISOTOPES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
CYCLOALKANES
DEUTERIUM COMPOUNDS
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HEPTANE
HYDROCARBONS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
HYPERFINE STRUCTURE
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
METHANOL
MOLECULAR STRUCTURE
MULTIPLETS
NITRILES
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SPECTRA
STABLE ISOTOPES
TERPENES
YIELDS