Nucleophilic addition of nitriles to secondary terpene alcohols
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), Vol. 56:7; Other Information: Translated from Zh. Obshch. Khim.; 56: No. 7, 1562-1566(Jul 1986)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
ALCOHOLS
ISOMERIZATION
AMIDES
CHEMICAL REACTION YIELD
INFRARED SPECTRA
NMR SPECTRA
NITRILES
AMINES
CARBON 13
CHEMICAL SHIFT
CHLOROFORM
COUPLING CONSTANTS
CYCLOALKANES
DEUTERIUM COMPOUNDS
HEPTANE
HYDROGEN 1
HYPERFINE STRUCTURE
J-J COUPLING
METHANOL
MOLECULAR STRUCTURE
MULTIPLETS
TERPENES
ALKANES
CARBON ISOTOPES
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
COUPLING
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOTOPES
LIGHT NUCLEI
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SPECTRA
STABLE ISOTOPES
YIELDS
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory