- Nitration of some di- and tri-nitrohalobenzenes with solid sodium nitrite in the presence of 18 crown 6
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1-Halo-4-R1-6-R2-2-nitrobenzenes 1a-d (where a : hal = F, R1 = NO2, R2=H; b: hal = Cl, R1 = NO2, R2 = H; c: hal = Cl, R1 = H, R2 = NO2 ; d: hal = Cl, R1 = CF3, R2 = NO2; ) and 1-chloro-2,4,6-trinitrobezene 1e were nitrated in methylene chloride with solid sodium nitrite in the presence of 18C6, and afforded the corresponding nitroderivatives 4-R1-6-R2-1,2-dinitrobenzenes 3a-c (where a: R1 = NO2, R2 = H; b: R1 = H, R2 = NO2; c: R1 = CF3, R2 = NO2; ) and 1,2,3,5-tetranitrobenzene 3d, respectively. The yields of this nucleophilic process depended on the number of nitro substituents and on the halogene type. UV-VIS and NMR spectra, TLC behaviour and pH-depending repartition in biphasic system water/methylene chloride of the synthecized compounds 3a-d are presented.
- Badea, Florin,Stoica, Alice,Ioni?ǎ, Petre,Cǎproiu, Miron T.,Constantinescu, Titus
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p. 351 - 356
(2007/10/03)
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- AMBIPHILIC FUROXAN RING. BENZOFUROXAN OXIDATION BY PERACID AND REDUCTION BY COPPER
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Monopersulfuric acid, trifluoroperacetic acid and hydrogen peroxide in polyphosphonic acid, or with selenium dioxide in t-butyl alcohol, or in tetramethylene sulfone have each oxidized benzofuroxan into o-dinitrobenzene.Monopersulfuric acid oxidized 4-nitrobenzofuroxan into 1,2,3-trinitrobenzene (80percent) and 4,6-dinitrobenzofuroxan into 1,2,3,5-tetranitrobenzene (99percent); hydrogen peroxide in polyphosphoric acid was moderately efficient for the latter oxidation.Copper in acidified ethanol transformed 4,6-dinitrobenzofuroxan into picramide quantitatively.
- Boyer, Joseph H.,Huang, Chrongbao
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p. 1233 - 1240
(2007/10/02)
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- Oxidation of Nitrobenzofuroxans
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Monoperoxosulphuric acid oxidized 4-nitrobenzofuroxan into 1,2,3-trinitrobenzene (80percent) and 4,6-dinitrobenzofuroxan into 1,2,3,5-tetranitrobenzene (100percent).
- Boyer, Joseph H.,Huang, Chorngbao
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p. 365 - 366
(2007/10/02)
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- Synthesis of Polynitro Compounds. Peroxydisulfuric Acid Oxidation of Polynitroarylamines to Polynitro Aromatics.
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Peroxydisulfuric acid in sulfuric acid solution, prepared by reaction of hydrogen peroxide with excess oleum or 100percent H2SO4, oxidizes primary polynitroarylamines and their N-acetamido derivatives to polynitro aromatics in good to excellent yields.The new procedure is illustrated by the synthesis of several new polynitro compounds, not preparable by known synthetic methods.Peroxytrifluoromethanesulfonic acid is comparably efficient for such oxidations.The scope and limitations of the new reaction have been examined and compared to other methods of synthesis of polynitro compounds.
- Nielsen, Arnold T.,Atkins, Ronald L.,Norris, William P.,Coon, Clifford L.,Sitzmann, Michael E.
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p. 2341 - 2347
(2007/10/02)
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