15513-52-7Relevant articles and documents
OXIDATIVE DEMETHYLATION OF SOME METHYLNITROPYRIDINE 1-OXIDES
Achremowicz, Lucjan
, p. 2433 - 2434 (1980)
3-Nitropyridine 1-oxide and 5-methyl-3-nitropyridine 1-oxide are produced readily by oxidative demethylation using SeO2 of 2-methyl- and 2,5-dimethyl-3-nitropyridine 1-oxides.
Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate
Natarajan, Palani,Chaudhary, Renu,Venugopalan, Paloth
, p. 10498 - 10504 (2015/11/18)
A novel and efficient method for the regioselective nitration of a series of aliphatic and aromatic carboxylic acids to their corresponding nitro compounds using nitronium tetrafluoroborate and silver carbonate in dimethylacetamide has been described. This transformation is believed to proceed via the alkyl-silver or aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerant of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology when compared to known methods for syntheses of nitroalkyls and nitroarenes.
Nitration of Aromatic and Heteroaromatic Compounds by Dinitrogen Pentaoxide
Bakke, Jan M.,Hegbom, Ingrid,Oevreeide, Elin,Aaby, Kjersti
, p. 1001 - 1006 (2007/10/02)
Nitration of benzene and monosubstituted benzenes in liquid SO2 by dinitrogen pentaoxide at - 11 deg C gave the corresponding nitroarenes with substitution patterns similar to those obtained by nitrations with HNO3-H2SO4.For acetophenone an o/m ratio of 0.94 was obtained.The yields were dependent on the substituents.With a 1:1 ratio of arene: N2O5 the yields varied from 73percent for toluene to 0.4percent for nitrobenzene as substrates.From competition experiments and the nitration of bibenzyl it was concluded that the reaction was faster than the macroscopic rate of mixing.The qualitative order of reactivity for PhX was X = OCH3>CH3>H>Cl>CH3CO>NO2.Nitration with N2O5 in liquid CO2 gave similar results.Nitration of pyrimidine, pyrrole, imidazole and indole with N2O5-SO2 gave no nitrated products.With thiophene, 2- (34percent) and 3-nitrothiophene (5percent) together with 2,4-(16percent) and 2,5-dinitrothiophene (8percent) were obtained.With pyridine, mono- and di-methylpyridines, quinoline, isoquinoline and 4-phenylpyridine nitration of the pyridine ring was obtained.The yields varied from ca. 70percent to 16percent, except for 3,5-, 2,5- and 2,6-dimethylpyridine for which only traces of nitro-dimethylpyridines were obtained.The reaction with the pyridines appears to be intramolecular both in the SO2 phase and in the water phase used for quenching the reaction.The reaction was proposed to proceed by a complex formed in liquid SO2: