- 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
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In the reaction of 1-nitronaphthalene witk K(18)OH and (16)O2 in liquid ammonia 1-nitro-2- and 4-nitro-1-naphthols labeled with the (18)O isotope in the hydroxyl group are formed.The ratio of the isomers and the content of the (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 (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 from the oxygen of the O2.
- Malykhin, E. V.,Shteingarts, V. D.
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p. 938 - 946
(2007/10/02)
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- REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. I. SUBSTITUTION OF HYDROGEN ATOM BY HYDROXY GROUP IN AROMATIC NITRO COMPOUNDS BY THE ACTION OF POTASSIUM HYDROXIDE AND OXYGEN
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The reaction of nitrobenzene and 1-nitro- and 1,5- and 1,8-dinitronaphthalenes with potassium hydroxide and oxygen in liquid ammonia at -33 deg C gives nitrophenols and nitro- and dinitronaphthols respectively, corresponding to substitution of the hydrogen atom of the hydroxy group at the ortho and para positions to the nitro group. 4-Nitro-3-hydroxybiphenyl was obtained from 4-nitrobiphenyl under analogous conditions.The reaction of 1-nitronaphthalene with potassium hydroxide and oxygen at -70 deg C is characterized by exclusive ortho entry of the hydroxy group in relation to the nitro group.
- Malykhin, E.V.,Shtark, A.A.,Shteingarts, V.D.
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p. 1661 - 1666
(2007/10/02)
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- SUBSTITUTION OF HYDROGEN ATOM IN THE AROMATIC RING BY A HYDROXY GROUP IN THE REACTION OF NITRONAPHTHALENES WITH POTASSIUM SUPEROXIDE
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The reaction of 1-nitro and 1,5- and 1,8-dinitronaphthalenes with potassium superoxide and oxygen in liquid ammonia or diglyme leads to the formation of mono- and dinitronaphthols respectively, corresponding to substitution of a hydrogen atom by a hydroxy group at the ortho and para positions in relation to the nitro group.In the reaction of the product from reduction of the nitronaphthalene by an equimolar amount of metallic potassium with oxygen 1,2- and 1,4-naphthoquinone oximes were obtained in addition to the nitronaphthols.
- Malykhin, E. V.,Shteingarts, V. D.
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p. 2146 - 2152
(2007/10/02)
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