- OXIDATION OF β-HYDROXYNITROSAMINES TO β-KETONITROSAMINES WITH KMnO4-METAL.SO4-XH2O IN NON-AQUEOUS MEDIA
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The oxidation of β-hydroxynitrosamines to the corresponding β-ketonitrosamine is reported.The reactions carried out in benzene or dichloromethane using powdered KMnO4-CuSO4.5H2O, or KMnO4-MgSO4.7H2O.Work-up of the reaction and purification of the product
- Saavedra, Joseph E.,Temu, Caroline T.,Farnsworth, David W.
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p. 215 - 220
(2007/10/02)
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- ONE-POT OXIDATION AND NITROSATION OF β-ALKANOLAMINES WITH KMnO4-NaNO2. A CONVENIENT PREPARATION OF β-KETONITROSAMINES
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The oxidation and nitrosation of β-alkanolamines to the corresponding β-ketonitrosamines is reported.The oxidation is carried out with potassium permanganate in acidic medium, followed by nitrosation of the protonated aminoketone, with sodium nitrite, to the corresponding β-ketonitrosamine.
- Pei, Guo-Kui,Farnsworth, David W.,Saavedra, Joseph E.
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p. 207 - 214
(2007/10/02)
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- Electrochemical Oxidation of N-Nitrosodialkylamines: Mechanism of N-Nitramine and β-Ketonitrosamine Formation
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Electrochemical oxidation of N-nitrosamines (1) derived from symmetrical dialkylamines was investigated in acetonitrile in the presence of dissolved oxygen.On cyclic voltammetry at ambient temperature, 1 showed two or three irreversible anodic peaks, depending upon the structure.Macroscale electrolysis, either controlled potential or constant current, of 1 which showed three voltammetric peaks gave the corresponding nitramine (2) and N-alkyl-N-(2-oxoalkyl)nitrosamine (3) as the main products.In the case of 1 which showed two voltammetric peaks, however, the side chain oxidized nitrosamine 3 was not obtained.It is suggested that the oxygen atom incorporated in the products 2 and 3 originated from dioxygen dissolved in the medium, and that the numbers of electrons required for the formation of 2 and 3 are one and two, respectively.A possible reaction sequence, which involves the reactions of the radical cation (4) derived from 1 and a radical formed by intramolecular rearrangement of 4 with dioxygen, is proposed.Keywords---N-nitrosodialkylamine; N-nitramine; N-alkyl-N-(2-oxoalkyl)nitrosamine; electrochemical oxidation; cyclic voltammetry; controlled potential electrolysis; constant current electrolysis
- Masui, Masaichiro,Nose, Koichi,Terauchi, Satomi,Yamakawa, Eiko,Jeong, Jisook,at al.
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p. 2721 - 2730
(2007/10/02)
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