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100-17-4Relevant articles and documents
Commercial Ion Exchange Resins as Catalysts in Solid-Solid-Liquid Reactions
Arrad, Onn,Sasson, Yoel
, p. 4993 - 4998 (1989)
Nucleophilic substitutions, base-catalyzed alkylations, and oxidation of a secondary alcohol have been carried out in a nonpolar solvent with inorganic solid reagents using polymer-bound quarternary ammonium or phosphonium catalysts.The products could be isolated simply by filtration and evaporation of the solvent.Some commercial ion exchange resins, which are known to be inactive in liquid-liquid systems, were found to have a similar or even superior activity in comparison with the usual "triphase catalysts".The resins were chemically stable under the reaction conditions, but their mechanical breakdown could be reduced only by application of unconventional means of agitation.
Reinterpretation of the kinetic data and the non-steady state hypothesis (two-step mechanism) for the SN2 reaction between p-nitrophenoxide and methyl iodide in aprotic solvents containing water
Humeres, Eduardo,Bentley, T. William
, p. 1969 - 1971 (2003)
Kinetic data obtained by conventional spectrophotometry for reaction of sodium p-nitrophenoxide with methyl iodide in degassed acetone are reported. The rate constants obtained from the first 10% of reaction do not differ significantly from those obtained over longer reaction times (e.g. 50% reaction)-the main criteria of Parker et al. (Org. Biomol. Chem., 2003, 1, 36-38) for a non-steady state two-step mechanism. Reactions are accelerated by crown ether, suggesting a mechanism via a free ion pair. Product studies by high performance liquid chromatography of reactions in aqueous acetonitrile (used by Parker et al.) show that the yield of methylated product is strongly affected by at least two base-neutralising side reactions.
Solid state S-methylation of thiols and O-methylation of phenols and naphthols with dimethyl sulfate under microwave irradiation
Heravi, Majid M.,Ahari, Neda Zamani,Oskooie, Hossein A.,Ghassemzadeh, Mitra
, p. 1701 - 1712 (2005)
Mild and efficient S-methylation of thiols and o-methylation of phenols and naphthals occurs with dimethyl sulfate (DMS) supported on basic alumina under microwave irradiation in solventless system. Copyright Taylor & Francis Inc.
Ionic liquid effect: Selective aniline oxidative coupling to azoxybenzene by TiO2
Qadir, Muhammad I.,Scholten, Jackson D.,Dupont, Jairton
, p. 1459 - 1462 (2015)
Simple commercially available TiO2 in ionic liquids (ILs) promotes the oxidative catalytic coupling of anilines to diazo compounds. For example, the reaction of aniline with molecular oxygen (5 bars) in the presence of TiO2 and functionalised imidazolium-based ILs affords azoxybenzene in up to 85% selectivity. The catalytic selectivity and activity are mainly related to the viscosity, oxygen solubility, and stability of the superoxide ion (O2-) and ionic species provided by the IL (IL effect). This effect is evident since most of the reactions performed in the presence of ILs gave as major products the azoxybenzene zwitterions. This is in opposition to that performed in toluene, which gave almost exclusively azobenzene.
Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration
Murai, Masahito,Nishinaka, Naoki,Kimura, Mizuki,Takai, Kazuhiko
, (2019)
Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing π-conjugated molecules.
Manganese-Catalyzed One-Pot Conversion of Nitroarenes into N-Methylarylamines Using Methanol
Mast, Nicolas,Morrill, Louis C.,Reed-Berendt, Benjamin G.
, (2020)
A manganese-catalyzed one-pot conversion of nitroarenes into N-methylarylamines has been developed. This transfer hydrogenation method employs a well-defined bench stable Mn PN3P pincer precatalyst in combination with methanol as both the reductant and the C1 source. A selection of commercially available nitroarenes was converted into N-methylarylamines in synthetically useful yields.
Copper-catalyzed protodecarboxylation of aromatic carboxylic acids
Goossen, Lukas J.,Thiel, Werner R.,Rodriguez, Nuria,Linder, Christophe,Melzer, Bettina
, p. 2241 - 2246 (2007)
A catalyst generated from copper(I) oxide and 4,7-diphenyl-l,10- phenanthroline for the first time allows the catalytic protodecarboxylation even of deactivated aromatic carboxylic acids, giving rise to the corresponding arenes. Based on DFT calculations, a reaction pathway is proposed that accurately reflects the experimental results, such as the observed reactivity order of the substrates.
Electrophilic nitration of aromatics in ionic liquid solvents
Laali,Gettwert
, p. 35 - 40 (2001)
Potential utility of a series of 1-ethyl-3-methylimidazolium salts [emim][X] with X = OTf-, CF3COO-, and NO3- as well as [HNEtPri2][CF3COO] (protonated Huenig's base) ionic liquids were explored as solvent for electrophilic nitration of aromatics using a variety of nitrating systems, namely NH4NO3/TFAA, isoamyl nitrate/BF3·Et2O, isoamyl nitrate/TfOH, Cu(NO3)/TFAA, and AgNO3/Tf2O. Among these, NH4NO3/TFAA (with [emim][CF3COO], [emim][NO3]) and isoamyl nitrate/BF3·Et2O, isoamyl nitrate/TfOH (with [emim][OTf]) provided the best overall systems both in terms of nitration efficiency and recycling/reuse of the ionic liquids. For [NO2][BF4] nitration, the commonly used ionic liquids [emim][AlCl4] and [emim][Al2Cl7] are unsuitable, as counterion exchange and arene nitration compete. [Emim][BF4] is ring nitrated with [NO2][BF4] producing [NO2-emim][BF4] salt, which is of limited utility due to its increased viscosity. Nitration in ionic liquids is surveyed using a host of aromatic substrates with varied reactivities. The preparative scope of the ionic liquids was also extended. Counterion dependency of the NMR spectra of the [emim][X] liquids can be used to gauge counterion exchange (metathesis) during nitration. Ionic liquid nitration is a useful alternative to classical nitration routes due to easier product isolation and recovery of the ionic liquid solvent, and because it avoids problems associated with neutralization of large quantities of strong acid.
The oxidation of azo dyes by peroxy acids and tert-butyl hydroperoxide in aqueous solution catalysed by iron(III) 5,10,15,20-tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin: Product studies and mechanism
Hodges, George R.,Smith, John R. Lindsay,Oakes, John
, p. 1943 - 1952 (1999)
Product studies on the oxidation of two 1-arylazo-2-hydroxynaphthalene-6-sulfonate dyes by peroxy acids and by tert-butyl hydroperoxide catalysed by iron(III) 5,10,15,20-tetra(2,6-dichloro-2-sulfonatophenyl)porphyrin in solution have been carried out. In
Sustainable heck-matsuda reaction with catalytic amounts of diazonium salts: An experimental and theoretical study
Susperregui, Nicolas,Miqueu, Karinne,Sotiropoulos, Jean-Marc,Lecallonnec, Francois,Fouquet, Eric,Felpin, Francois-Xavier
, p. 7210 - 7218 (2012)
The palladium-catalyzed Heck-Matsuda reaction with a catalytic amount of an in-situ-generated diazonium salt proceeded under mild and sustainable conditions. The reaction proceeded at room temperature, under base-free conditions, and only generated tBuOH, H2O, and N2 as by-products. Ortho-substituted diazonium salts were more-efficiently coupled to methyl acrylate than their corresponding paraisomers, which required the addition of anisole as an additive. In support of these experimental data, we carried out theoretical studies to gain a deeper understanding of these reaction outcomes.