Reaction of aromatic compounds with nucleophilic reagents in liquid ammonia. IX. Reaction of polyfluorinated derivatives of benzene with sodium amide
Under the influence of sodium amide in liquid ammonia at a temperature no higher than /minus/33/degree/C pentafluorobenzene, 1,2,4,5-tetrafluorobenzene, and 1,3-difluorobenzene undergo deprotonation with the formation of fluorinated phenyl anions, which are resistance to the elimination of a fluoride ion and can be detected by the formation of the products from interaction with electrophiles (with the initial compound in the first case and with methyl iodide in the other two cases). 1,3,5-Trifluorobenzene behaves similarly in reaction with one equivalent of sodium amide, but with two equivalents of sodium amide this compound and 1,2,3,5-tetrafluorobenzene undergo substitution of a fluorine atom by an amino group with the formation of 3,5-di- and 3,4,5-trifluoroanilines respectively. This is clearly due to the double deprotonation of these compounds with the formation of polyfluorinated m-phenylene dianions, which are then converted with the elimination of a fluoride ion into the corresponding dehydrophenyl anions.
- Research Organization:
- Novosibirsk Institute of Organic Chemistry, (USSR)
- OSTI ID:
- 6046925
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:12; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALKALI METAL COMPOUNDS
AMIDES
AMINATION
AMINES
AMMONIA
ANIONS
AROMATICS
ARYL RADICALS
CHARGED PARTICLES
CHEMICAL REACTIONS
DEHYDROGENATION
ENERGY
FLUORINATED AROMATIC HYDROCARBONS
FLUORINATION
FLUORINE 19
FLUORINE ISOTOPES
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HYDRIDES
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
IODINATED ALIPHATIC HYDROCARBONS
IONS
ISOTOPES
LIGHT NUCLEI
METHYL IODIDE
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PH VALUE
PHENYL RADICALS
RADICALS
SODIUM COMPOUNDS
SOLVENT PROPERTIES
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS