Reactions of aromatic hydrocarbons with nucleophilic reagents in liquid ammonia. VII. Direction of hydroxylation of 3-substituted (Cl, Br, I, NO/sub 2/) nitrobenzenes with potassium hydroxide (in Russian)
The reaction of 3-chloro-, 3-bromo-, and 3-iodonitrobenzenes with potassium hydroxide and oxygen in liquid ammonia (-33/sup 0/C) leads to the formation of nitrohalogenophenols, corresponding to substitution of the hydrogen atom at the ortho and para positions of the ring in relation to the nitro group by a hydroxy group. In the case of the last two substrates it also leads to the corresponding 2-halo-geno-3',4'-dinitrodiphenylamines. In view of the fact that substituted diphenylamines are formed under the same conditions as a result of the reaction of 3-nitro-aniline with 3-halogenonitrobenzenes it is suggested that 3-bromo- and 3-iodonitrobenzenes are partly converted into 3-nitroaniline through the intermediate formation of 3-nitrodehydrobenzene. During dehydroxylation in the absence of oxygen the proportion of the phenols corresponding to substitution of the hydrogen atom at the para position to the nitro group by the hydroxy group increases, and the degree of transformation of the initial compounds decreases. 2,4-dinitrophenol is formed with a low yield during the reaction of 1,3-nitrobenzene and potassium hydroxide in the presence of oxygen or in an atmosphere of argon.
- Research Organization:
- Novosibirsk Institute and Organic Chemistry, USSR
- OSTI ID:
- 6388102
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 22:4; Other Information: Translated from Zh. Org. Khim.; 22: No. 4, 806-814(Apr 1986)
- Country of Publication:
- United States
- Language:
- Russian
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ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
BROMINATED AROMATIC HYDROCARBONS
HYDROXYLATION
CHLORINATED AROMATIC HYDROCARBONS
IODINATED AROMATIC HYDROCARBONS
NITRO COMPOUNDS
SYNTHESIS
NITROBENZENE
PHENOLS
POTASSIUM HYDROXIDES
ACTIVATION ENERGY
CATALYTIC EFFECTS
AMINES
AMMONIA
ARGON
CATALYSTS
CHEMICAL REACTION KINETICS
CHEMICAL SHIFT
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
J-J COUPLING
NMR SPECTRA
ALKALI METAL COMPOUNDS
AROMATICS
COUPLING
ELEMENTS
ENERGY
FLUIDS
GASES
HALOGENATED AROMATIC HYDROCARBONS
HYDRIDES
HYDROGEN COMPOUNDS
HYDROXIDES
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
KINETICS
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NONMETALS
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
POTASSIUM COMPOUNDS
RARE GASES
REACTION KINETICS
SPECTRA
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory