- 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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- Transformations of Cyclohexanone Oxime into gem-Dinitrocyclohexane
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In reaction of cyclohexanone oxime with various electrophilic agents, the highest yields of gem-dinitrocyclohexane were obtained with N2O5 and O3 as oxidants and HNO3 in (CH3CO)2O as a nitrating agent.
- Moiseev,Nafikov,Makarova
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p. 607 - 608
(2007/10/03)
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- Radical-Nucleophilic (SRN1) Reactions. Part 4. Preparation, Reactions, and Electron Spin Resonance Studies of α-Nitro Azides
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2-Azido-2-nitropropane and 1-azido-1-nitrocyclohexane have been prepared by syntheses involving intermediate radical-anions (SRN1 and oxidative addition).SRN1 Reactions between α-nitroazides and azide, benzenesulphinate, and p-chlorobenzenethiolate proceed with loss of nitrite.The SRN1 reaction between 1-azido-1-nitrocyclohexane and the anion of 2-nitropropane proceeds with loss of azide.Reactions between 2-azido-2-nitropropane and the anions of 2-nitropropane and diethyl ethylmalonate yield oxidative dimerisation.E.s.r. spectroscopy has been used to observe electron-capture by 2-azido-2-nitropropane and its dissociation to nitrite and an ill-defined radical which may be (Me2CN3)..The addition of benzenesulphinate and the anion of 2-nitropropane to Me2C.NO2, formed by a minor dissociation route from 2C(N3)NO2>-., has been observed by e.s.r. spectroscopy.
- Al-Khalil, Suleiman I.,Bowman, W. Russell,Symons, Martyn C. R.
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p. 555 - 566
(2007/10/02)
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- Catalyzed Oxidative Nitration of Nitronate Salts
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Nitronate salts are converted to gem-dinitro compounds with nitrite ion and persulfate, in the presence of a catalytic amount of ferricyanide.The use of cyanide or sulfinate salts in place of nitrile gave gem-cyanonitro compounds and α-nitro sulfones, respectively.
- Garver, Lee C.,Grakauskas, V.,Baum, Kurt
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p. 1699 - 1702
(2007/10/02)
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- Oxidative Substitution of Nitroparaffin Salts
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α,α-Dinitro compounds, α-nitro sulfones, and α-nitro nitriles are obtained in excellent yields when nitroparaffin salts are coupled to nitrite, benzenesulfinate, and cyanide ions by the agency of potassium ferricyanide.
- Kornblum, Nathan,Singh, Haribansh K.,Kelly, William J.
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p. 332 - 337
(2007/10/02)
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