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Reaction of aromatic compounds with nucleophilic reagents in liquid ammonia. VIII. The origin of the oxygen atom of the hydroxy group in the products from the hydroxylation of 1-nitronaphthalene with alkali and molecular oxygen

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:7160573
;
In the reaction of 1-nitronaphthalene with K/sup 18/OH and /sup 16/O/sub 2/ in liquid ammonia 1-nitro-2- and 4-nitro-1-naphthols labeled with the /sup 18/O isotope in the hydroxyl group are formed. The ratio of the isomers and the content of the /sup 18/O isotope depend on the ratio of 1-nitronaphthalene and alkali, on the temperature, and on the presence of moisture in the ammonia. The amount of the /sup 18/O isotope in the hydroxylation products indicates that in contrast to the analogous reaction of nitrobenzene and its derivatives the hydroxy function of the products in this case is formed not only from the alkali but also to a significant degree form the oxygen of the O/sub 2/.
Research Organization:
Novosibirsk Institute of Organic Chemistry (USSR)
OSTI ID:
7160573
Journal Information:
J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:5; ISSN JOCYA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400101* -- Activation
Nuclear Reaction
Radiometric & Radiochemical Procedures
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ACTIVATION ENERGY
ALKALI METAL COMPOUNDS
AMMONIA
AROMATICS
CHEMICAL ANALYSIS
CHEMICAL REACTION KINETICS
CHEMICAL SHIFT
CONDENSED AROMATICS
COUPLING
COUPLING CONSTANTS
ELEMENTS
ENERGY
EVEN-EVEN NUCLEI
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
HYDROXY COMPOUNDS
HYDROXYLATION
INTERMEDIATE COUPLING
ISOMERS
ISOTOPE RATIO
ISOTOPES
J-J COUPLING
KINETICS
LABELLED COMPOUNDS
LIGHT NUCLEI
MASS SPECTRA
NAPHTHALENE
NAPHTHOLS
NITRO COMPOUNDS
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NMR SPECTRA
NONMETALS
NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN
OXYGEN 16
OXYGEN 18
OXYGEN COMPOUNDS
OXYGEN ISOTOPES
PHENOLS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
QUANTITATIVE CHEMICAL ANALYSIS
RADIOACTIVITY
RADIOCHEMICAL ANALYSIS
REACTION KINETICS
SPECTRA
STABLE ISOTOPES
SYNTHESIS
TEMPERATURE DEPENDENCE