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

Journal Article · Sat Sep 20 04:00:00 EDT 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6388102

Malykhin, E V; Kolesnichenko, G A; Shteingarts, V D

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), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:4; ISSN JOCYA
• Country of Publication: United States
• Language: Russian

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ACTIVATION ENERGY
ALKALI METAL COMPOUNDS
AMINES
AMMONIA
ARGON
AROMATICS
BROMINATED AROMATIC HYDROCARBONS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL SHIFT
CHLORINATED AROMATIC HYDROCARBONS
COUPLING
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
ELEMENTS
ENERGY
FLUIDS
GASES
HALOGENATED AROMATIC HYDROCARBONS
HYDRIDES
HYDROGEN COMPOUNDS
HYDROXIDES
HYDROXY COMPOUNDS
HYDROXYLATION
INTERMEDIATE COUPLING
IODINATED AROMATIC HYDROCARBONS
J-J COUPLING
KINETICS
NITRO COMPOUNDS
NITROBENZENE
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NMR SPECTRA
NONMETALS
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
PHENOLS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
RARE GASES
REACTION KINETICS
SPECTRA
SYNTHESIS