- N-methyl-2-chloropyridinium iodide/NaNO2/Wet SiO2: Neutral reagent system for the nitration of activated aromatic compounds under very mild conditions
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Mononitration of activated aromatic compounds using N-methyl-2-chloro-pyridinium iodide (Mukaiyama reagent)/NaNO2/wet SiO2 reagent system under neutral, very mild and environmentally safer reaction condition has been developed. Various structurally diverse aromatic rings are subjected in this condition and the corresponding nitro-aromatic compounds are prepared in moderately high yields.
- Azadi, Roya,Nazari-Far, Zahra
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p. 136 - 140
(2015/06/22)
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- Hydroxylation of nitrated naphthalenes with KO2/crown ether
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Superoxide radical anion (O2/·-), generated by KO2/crown ether, is effective for hydroxylation of nitronaphthalenes. When mono- and di-nitronaphthalenes are treated with KO2/crown ether, hydroxylation results at
- Fukuhara,Hara,Nakanishi,Miyata
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p. 1532 - 1535
(2007/10/03)
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- Specific para-hydroxylation of nitronaphthalenes with cumene hydroperoxide in basic aqueous media
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A synthetic method for specific para-hydroxylation of nitroarenes has been developed. The reaction of nitronaphthalenes with cumeme hydroperoxide in basic aqueous media produces exclusively para-hydroxy nitronaphthalenes in good yield. The selectivity of ortho and para hydroxylation is mediated by water content. The rationale for water-controlled orientation of hydroxylation has been briefly discussed. (C) 2000 Elsevier Science Ltd.
- Zhu, Lei,Zhang, Lin-Hua
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p. 3519 - 3522
(2007/10/03)
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- Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen
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Rhone-Poulenc Polska Ltd., ul. Grzybowska 80/82, 00-844 Warszawa, Poland Garbo- and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.
- Makosza, Mieczyslaw,Sienkiewicz, Krzysztof
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p. 4199 - 4208
(2007/10/03)
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- Kinetics and mechanism of ammonolysis and alkaline hydrolysis of naphthyl acetates in aqueous medium: Part 1 - 4-Substituted 1-naphthyl acetates
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A series of 4- substituted 1-naphthyl acetates have been prepared. The kinetics of their ammonolysis have been followed at 20°, 25° and 30°C under pseudo-first order conditions at different pH in water containing 1% dioxan at an ionic strength of 1.0 mol dm-3. The possible mechanisms suggest the existence of general base catalysis for 4-methyl-1-naphthyl acetate. For esters with electron-withdrawing substituents, ammonolysis proceeds through an unassisted simple nucleophilic substitution pathway. The alkaline hydrolysis of all the esters is also followed under identical reaction conditions.
- Ananthakrishna Nadar,Rajarathinam
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p. 749 - 753
(2007/10/03)
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- Reactions of Aromatic Compounds with Nucleophilic Reagents in Liquid Ammonia. XV. Hydroxylation of Aromatic Nitro Compounds with Potassium Peroxide
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Reactions of 1-nitro- and 1,8-dinitronaphthalenes with K2O2 in liquid ammonia at -33°C yield, respectively, mono- and dinitronaphthols. The ratio of the products with 1,2- and 1,4-arrangement of the nitro and hydroxy groups is 1:(1.0-1.3). Lowering the temperature to -60°C results in almost exclusive formation of the 1,4-isomers. Hydroxylation of 1,5-dinitronaphthalene by the action of K2O2 occurs both at the ortho and para positions with respect to the nitro group only in the presence of oxygen. Reactions of 4-chloronitrobenzene and 1,4-dinitrobenzene with K2O2 afford 4-nitrophenol in high yield, whereas nitrobenzene, 4,4′-dinitrobiphenyl, and 1,3-dinitrobenzene do not undergo hydroxylation by the action of K2O2 in liquid ammonia both under argon and in the presence of oxygen.
- Malykhin,Shteingarts
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p. 636 - 643
(2007/10/03)
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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
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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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- Nitrocyclohexadienones : a new class of nitrating agents
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Various nitrocyclohexadienones are proposed as new nitrating agents. These compounds are easy to prepare from corresponding phenols, easy to handle and stable. Nitrocyclohexadienones act as nitronium carriers using rearomatization as the driving force and permit nitration of highly activated substrates under mild conditions and with good yields.
- Lemaire, Marc,Guy, Alain,Roussel, Jacques,Guette, Jean-paul
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p. 835 - 844
(2007/10/02)
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- NITROCYCLOHEXADIENONES : CONVENIENT NEW MONO-NITRATING AGENTS FOR AROMATIC COMPOUNDS
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Nitrocyclohexadienones are effective nitrating agents for naphtols in dry ether at room temperature to give good yields of mononitrated products.
- Roussel, J.,Lemaire, M.,Guy, A.,Guette, J.P.
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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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