Isomeric composition of the products from the reaction of poly- and perfluoro-1-alkenes with alkali-metal fluorides in aprotic solvents
The reaction of normal perfluoro-1-alkenes with alkali-metal fluorides in polar aprotic solvents was investigated, and the isomeric composition of the products was determined. The rearrangement of perfluorinated olefins catalyzed by the fluoride ion is stereoselective and leads to the preferential formation of the trans isomers of internal perfluoroalkenes. This is explained from the standpoint of a carbanionic mechanism. The /sup 19/F NMR spectra of the cis and trans isomers of the perfluoroalkenes were obtained, and their relationships are discussed. For the cis isomers the signals of all the groups in the /sup 19/F NMR spectrum are observed in the downfield region from the corresponding signals of the trans isomers. This effect is strongest for substituents situated directly at the double bond.
- Research Organization:
- Institute of Chemistry, Sverdlovsk (USSR)
- OSTI ID:
- 6364906
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:9; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
ALKENES
BROMINATED ALIPHATIC HYDROCARBONS
CATALYSIS
CATALYTIC EFFECTS
CESIUM COMPOUNDS
CESIUM FLUORIDES
CHEMICAL REACTIONS
COUPLING
COUPLING CONSTANTS
DOUBLE RESONANCE METHODS
FLUORIDES
FLUORINATED ALIPHATIC HYDROCARBONS
FLUORINE 19
FLUORINE COMPOUNDS
FLUORINE ISOTOPES
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
INTERMEDIATE COUPLING
ISOMERIZATION
ISOMERS
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SOLVENTS
POTASSIUM COMPOUNDS
POTASSIUM FLUORIDES
SOLVENTS
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY