- New reagent for a one-step synthesis of gem-chloronitro compounds from oximes
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The use of chlorine bleach (5% NaOCl) for the halogenation-oxidation of oximes to gem-chloronitro compounds is reported. Chlorine bleach afforded satisfactory yields when employed alone either at room temperature or under ultrasonic irradiation.
- Zolfigol,Khazaei,Kolvari,Koukabi,Gilandoust
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experimental part
p. 1058 - 1062
(2012/02/06)
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- Oxidation of gem-chloronitroso- and vic-chloronitroso-alkanes and -cycloalkanes to respective chloronitro compounds by novel cetyltrimethylammonium hypochlorite reagent
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Cetyltrimethylammonium hypochlorite (CTAHC) is prepared and used as an oxidizing agent for nitroso group to nitro group. The gem-chloronitroso and vic-chloronitroso compounds are prepared respectively from ketoximes and olefins by reacting with NOCl generated in situ from chlorotrimethylsilane (TMSC1 (l) and iso-amyl nitrite. CTAHC oxidizes gem-chloronitroso and vic-chloronitroso compounds to the corresponding chloronitro derivatives. While gem-chloronitro compounds are obtained in good yields, the vic-chloronitro derivatives are formed in moderate yields, because of the propensity of the vic-chloronitroso group to tautomerize to α-chlorooxime. The present method is simple and practical, particularly for the preparation of vic-chloronitro compounds, considering the fact that the known methods of their preparation are few and quite involved. Indian Academy of Sciences.
- Mohammed, Abdulkarim H.A.,Nagendrappa, Gopalpur
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p. 433 - 441
(2012/03/26)
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- Generation of nitryl chloride from chlorotrimethylsilane-acetyl nitrate reaction: A one-pot preparation of gem-chloronitro compounds from oximes
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While iso-amyl nitrite reacts with chlorotrimethylsilane to give NOCl, iso-amyl nitrate does not yield NO 2Cl with silicon reagent. However, acetyl nitrate reacts successfully with chlorotrimethylsilane to give nitryl chloride, which is charact
- Mohammed, Abdulkarim H. A.,Nagendrappa, Gopalpur
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experimental part
p. 571 - 577
(2010/12/20)
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- Chlorination of oximes with aqueous H2O2/HCl system: Facile synthesis of gem-chloronitroso- and gem-chloronitroalkanes, gem-chloronitroso- and gem-chloronitrocycloalkanes
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Chlorination of cyclic and linear ketone oximes with aqueous H 2O2/HCl in a two-phase dichloromethane-water system selectively affords gem-chloronitroso compounds in yields of up to 94%. One-pot oxidation of the resulting gem-chloronitroso compounds with peracetic acid, prepared in situ, gives gem-chloronitroalkanes and cycloalkanes in yields of up to 82%. The advantages of the method are that it is facile and environmentally benign and does not require gaseous chlorine. Georg Thieme Verlag Stuttgart.
- Terent'ev, Alexander O.,Krylov, Igor B.,Ogibin, Yuri N.,Nikishin, Gennady I.
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p. 3819 - 3824
(2008/02/09)
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- Electrooxidative coupling of salts of nitro compounds with halide, nitrite, cyanide, and phenylsulfinate anions
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Electrolysis of salts of primary and secondary nitro compounds (nitroethane, 1- and 2-nitropropanes, nitrocyclohexane, and nitrocycloheptane) in the presence of excess halide, nitrite, cyanide, and phenylsulfinate anions under undivided and divided amperostatic electrolysis conditions in a two-phase medium (CH2Cl2/H2O) produces geminal nitrohalides (35-85% yields), dinitro compounds (15-51%), nitronitriles (6-27%), and nitrosulfones (50-70%). The salts of secondary nitro compounds form the products of oxidative coupling with halide and phenylsulfinate anions under the undivided electrolysis conditions. In all other cases, divided electrolysis is required.
- Ilovaisky,Merkulova,Ogibin,Nikishin
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p. 1585 - 1592
(2007/10/03)
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- A new method for the one-step conversion of oximes into gem-halo-nitro derivatives
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A mild and efficient process for one-step conversion of oximes into gem- halo-nitro compounds using Oxone and sodium chloride or potassium bromide is described.
- Curini, Massimo,Epifano, Francesco,Marcotullio, Maria Carla,Rosati, Ornelio,Rossi, Monia
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p. 6211 - 6218
(2007/10/03)
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- Synthesis of α-Chloronitro Compounds
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Treatment of acetone oxime, cyclohexanone oxime, bicyclo[3.3.1]nonane-2,6-dione dioxime, 2-adamantanone oxime, and 1,3-dicarboxyadamantane-2,6-dione dioxime with a mixture of hydrochloric acid and 30 percent hydrogen peroxide gave 2-chloro-2-nitropropane, 1-chloro-1-nitrocyclohexane, 2,6-dichloro-2,6-dinitrobicyclo[3.3.1]nonane, 2-chloro-2-nitroadamantane, and 2,6-dichloro-2,6-dinitroadamantane-1,3-dicarboxylic acid.
- Moiseev, I. K.,Mratkhuzina, T. A.,Makarova, N. V.
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p. 1777 - 1778
(2007/10/03)
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- One-step conversion of oximes to gem-chloro-nitro derivatives
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a new method for one-pot conversion of oximes to gem-chloro-nitro compounds using Oxone and sodium chloride is described.
- Ceccherelli, Paolo,Curini, Massimo,Epifano, Francesco,Marcotullio, Maria Carla,Rosati, Ornelio
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p. 4385 - 4386
(2007/10/03)
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- New Reagents for the Synthesis of gem-Halonitro Compounds from Oximes
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The utility of the N-haloheterocycles 1-sodio-3,5-dichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (4), 1,3,5-trichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (5), 1,3-dibromo-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (6), and 1,3-dibromo-5,5-dimethylhydantoin (
- Walters, Thomas R.,Zajac, Walter W.,Woods, James M.
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p. 316 - 321
(2007/10/02)
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- OXIDATIVE CONVERSION OF ALIPHATIC NITROCOMPOUNDS TO CARBONYLS USING SODIUM CHLORITE
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Aliphatic Nitrocompounds are converted to corresponding Carbonyls by means of Sodium Chlorite under phase transfer catalysis conditions (CH2Cl2-NaOH-1N-Bu4NHSO4).Primary nitrocompounds give aldehydes while secondary nitroalkanes give ketones in good yields.
- Ballini, Roberto,Petrini, Marino
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p. 5329 - 5332
(2007/10/02)
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- A Convenient Method For The Preparation of gem-Halonitro Compounds
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Aliphatic nitro compounds are easily halogenated by N-chloro- or N-bromosuccinimide in protic solvents to give the practically pure gem-halonitro compounds.
- Amrollah-Madjdabadi, A.,Beugelmans, R.,Lechevallier, A.
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p. 828 - 830
(2007/10/02)
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- AN EFFECTIVE AND MILD METHOD FOR THE CONVERSION OF OXIMES TO SECONDARY NITRO COMPOUNDS
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A mild and efficient process for the conversion of cyclic ketones to staurated nitro compounds, as outlined in eq. 1 below, is described.
- Corey, E. J.,Estreicher, Herbert
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p. 1117 - 1120
(2007/10/02)
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