19613-87-7Relevant academic research and scientific papers
Highly selective and controllable synthesis of arylhydroxylamines by the reduction of nitroarenes with an electron-withdrawing group using a new nitroreductase BaNTR1
Nguyen-Tran, Hieu-Huy,Zheng, Gao-Wei,Qian, Xu-Hong,Xu, Jian-He
supporting information, p. 2861 - 2864 (2014/03/21)
A new bacterial nitroreductase has been identified and used as a biocatalyst for the controllable reduction of a variety of nitroarenes with an electron-withdrawing group to the corresponding N-arylhydroxylamines under mild reaction conditions with excellent selectivity (>99%). This method therefore represents a green and efficient method for the synthesis of arylhydroxylamines.
Green-light photocatalytic reduction using dye-sensitized TiO2 and transition metal nanoparticles
Fueldner, Stefan,Mild, Ralph,Siegmund, Heiko Ingo,Schroeder, Josef A.,Gruber, Michael,Koenig, Burkhard
experimental part, p. 400 - 406 (2010/08/06)
Nitrobenzenes are cleanly reduced to anilines using Ru-sensitized TiO 2 photocatalysts and green light irradiation, if very small amounts of transitions metal salts are added, which form metal nanoparticles of narrow size distribution under the experimental conditions. The catalyst system is prepared by simple mixing of the components and is therefore easy to apply in organic synthesis. As light sources, commercial high power LEDs or sunlight are used. We report the optimization of the reaction conditions, the effect of trace amounts of added metal salts and demonstrate the use of green light photoreduction in the conversion of several nitrobenzene derivatives.
Carbon supported Pt colloid as effective catalyst for selective hydrogenation of nitroarenes to arylhydroxylamines
Rong, Zeming,Du, Wenqiang,Wang, Yue,Lu, Lianhai
supporting information; experimental part, p. 1559 - 1561 (2010/06/12)
The Pt colloid supported on carbon is an active and selective catalyst for the partial hydrogenation of nitroaromatics with electron-withdrawing substituents to the corresponding N-arylhydroxylamine, indicating an additive-free green catalytic approach fo
Effect of substituents on the rate of oxidation of anilines with peroxomonosulfate monoanion (HOOSO3-) in aqueous acetonitrile: A mechanistic study
Meenakshisundaram, Subbiah,Selvaraju,Made Gowda,Rangappa, Kanchugarakoppal S.
, p. 649 - 657 (2007/10/03)
Mechanistic studies on the oxidation of 18 meta-, para-, and ortho-substituted anilines (Ans) by HOOSO3- in aqueous acetonitrile medium have been performed. The reaction can be characterized by the experimental rate equation, -d[HSO5-]/dt = k[An][HSO5-] The addition of p-toluenesulfonic acid (TsOH) retards the reaction. The increase in the reactivity of anilines as the medium is made more aqueous is interpreted. The reaction is enhanced by electron-donating groups on the amine in the series consistent with the rate-limiting nucleophilic attack of the amine on the persulfate oxygen. The proposed mechanism involves the conversion of phenylhydroxylamine to nitrosobenzene in a fast step. The ESR study reveals the absence of free radicals in the reaction. Various attempts have been made to analyze the experimental rate constants in terms of LFER plots. Improved correlations are obtained with σ- values and the σ- form of the Yukawa-Tsuno equation.
A novel strategy for the preparation of arylhydroxylamines: Chemoselective reduction of aromatic nitro compounds using bakers' yeast
Li, Feng,Cui, Jingnan,Qian, Xuhong,Zhang, Rong
, p. 2338 - 2339 (2007/10/03)
Using bakers' yeast as a biocatalyst, the chemoselective reduction of aromatic nitro compounds bearing electron-withdrawing groups gave the corresponding hydroxylamines with good to excellent conversion under mild conditions.
Mechanism and reactivity in perborate oxidation of anilines in acetic acid
Karunakaran, Chockalingam,Kamalam, Ramasamy
, p. 2011 - 2018 (2007/10/03)
Perborate but not percarbonate in acetic acid generates peracetic acid on standing and the peracetic acid oxidation of anilines is fast. The oxidation with a fresh solution of perborate in acetic acid is smooth and second order but the specific oxidation rate increases with increasing [perborate]0 or [boric acid]. Perborate on dissolution affords hydrogen peroxide and a borate; the latter assists the former in the oxidation. The oxidation rates of anilines under identical conditions do not conform to any of the linear free energy relationships but the reaction rates of molecular anilines do. Perborate oxidation proceeds via two reaction paths but the overall oxidation rates of molecular anilines conform to structure reactivity relationships; the transition states do not differ significantly. Analysis of the oxidation rates of perborate and percarbonate reveals that while perborate oxidation is faster than percarbonate it is at least as selective as the latter.
Reaction of N-Acyloxy-2-nitrobenzenamines.I. Thermolysis in Benzene or Bromobenzene
Bryant, Ian R.,Dyall, Leonard K.
, p. 2275 - 2288 (2007/10/02)
N-Acyloxy-2-nitro- and N-acyloxy-2,4-dinitro-benzenamines have been pyrolysed at 140 deg C in benzene or bromobenzene solution.Homolysis ( to form RCO2-radical and ArNH-radical) is ruled out since virtually all the carboxylate is isolated as carboxylic acid.This acid might arise via a concerted elimination process ( the other product being a benzofurazan 1-oxide), or via heterolysis to ArNH01+, RCO21- with subsequent transfer of proton, and cyclization of the singlet 2-nitrophenylnitrene.These simple reactions compete with bimolecular reactions of products with substrate, in which the corresponding amine, azoxy compound and acid anhydride are generated.Attempts to synthesize N-tosyloxy derivatives of nitrobenzenamines gave only thermal decomposition products.N-Trifluoroacetoxy-2,4-dinitrobenzenamine was isolated as a crude product which detonated violently.
