- An efficient method for the oxidation of sulfides to sulfones
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Ruthenium trichloride - sodium periodate is a highly efficient and powerful system for the oxidation of unreactive sulfides to sulfones.
- Su, Weiguo
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- Synthesis of symmetrical diaryl sulfone by homocoupling of sodium arylsulfinate
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An efficient practical homocoupling reaction of sodium arylsulfinate promoted by Cu(II) is reported whereby symmetrical diaryl sulfone derivatives are obtained with high selectivity and reactivity by intermolecular cross-coupling. This homocoupling reacti
- Peng, Yao
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- Selective synthesis of sulfoxides and sulfones by methyltrioxorhenium-catalyzed oxidation of sulfides with hydrogen peroxide
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Methyltrioxorhenium-catalyzed oxidation of sulfides with hydrogen peroxide in ethanol has been found to be an efficient catalytic system for the selective formation of sulfoxides and sulfones. The oxidation using an equimolar amount of hydrogen peroxide afforded sulfoxides in excellent yield, and the use of two molar amounts of hydrogen peroxide gave sulfones quantitatively. Strongly deactivated sulfide, bis(4-nitrophenyl) sulfide, was converted smoothly to the corresponding sulfoxide and sulfone in excellent yields. The functional group in the side chain of sulfide such as a carbon-carbon double bond was not affected under the reaction conditions, and the sulfur atom was selectively oxidized.
- Yamazaki, Shigekazu
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- Tris(hydroxymethyl)aminomethane modified layered double hydroxides greatly facilitate polyoxometalate intercalation
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Polyoxometalate (POM) intercalation to layered double hydroxides (LDHs) has been greatly restricted by the geometry, charge and size of POMs. We report herein, for the first time, the intercalation of Na3[PW12O40]·15H2O into tris(hydroxymethyl)-aminomethane (Tris) modified layered double hydroxides (Tris-LDH-CO3) using an ion exchange method, resulting in the formation of novel intercalated Tris-LDH-PW12 under ambient conditions without the necessity of degassing CO2. Theoretical calculations show the decreased energy and the slightly distorted LDH layer after Tris modification, indicating that the Tris-modified LDH layers greatly facilitate the intercalation of PW12. Further application of Tris-LDH-PW12 for oxygenation of sulfides shows highly efficient and selective catalytic activities under mild conditions. The Tris-LDH-PW12 can be easily recovered and reused for more than 10 times without any obvious decrease of reactivity. This opens a completely new pathway for engineering POM-LDH advanced functional materials. This journal is
- Chen, Yang,Yan, Dongpeng,Song, Yu-Fei
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- Synthetic method of diarylsulfone compound
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The invention relates to a synthetic method of a diarylsulfone compound. The method is characterized in that a copper complex and aryl sulfonyl hydrazide are dissolved in an organic solvent, air serves as an oxidizing agent, a reaction is conducted at the room temperature, separation and purification are conducted to obtain the corresponding diarylsulfone compound, the molar ratio of the copper complex to the aryl sulfonyl hydrazide is (0.01-0.03):1.0, and the reaction time is 2-5 h. Compared with the prior art, the synthesis process provided by the invention has excellent selectivity and highyield, the catalyst copper complex in the reaction can catalyze the self-coupling of aryl sulfonyl hydrazide to synthesize the diarylsulfone compound at room temperature, and the reaction has the characteristics of mild and simple conditions, wide substrate range, convenient product separation, high reaction efficiency and the like.
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Paragraph 0029; 0033-0036
(2020/10/04)
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- An Efficient Oxidation of Sulfides to Sulfones with Urea-Hydrogen Peroxide in the Presence of Phthalic Anhydride in Ethyl Acetate
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A metal-free, environmentally benign oxidation of substituted sulfides directly to their corresponding sulfones is described. Using urea-hydrogen peroxide and phthalic anhydride in ethyl acetate clean conversion into the sulfone was achieved without observation of the possible sulfoxide oxidation product.
- Lutz, Marlon,Wenzler, Marta,Likhotvorik, Igor
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supporting information
p. 2231 - 2234
(2018/04/16)
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- PROCESS FOR THE PREPARATION OF SULFONAMIDE COMPOUNDS
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Process for the preparation of known sulfonamides having antibacterial activity applicable on industrial scale, which allows their production in high yields and purity, comprising in particular the step of nucleophile aromatic substitution and oxidation in suitable conditions.
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- TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides
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Figure presented. 1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6- tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Sheikh Arabi, Mehdi
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supporting information; experimental part
p. 6208 - 6213
(2010/11/04)
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- Oxidation kinetics of some sulfoxides with N,N-dibromobenzene sulfonamide
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The kinetics of oxidation of some sulfoxides with dibromamine-B yielding sulfones was investigated in presence of HgII, and the rate equation, kobs = k3K2K′h[S]/[RNH 2] + K′h was found to be valid. The reaction involves two distinct pathways namely initial fast step and a subsequent slow step. The chloride ions have no effect on the reactivity of sulfoxides. Sulfoxides containing electron-attracting substituents retard the reactivity while those containing electron-releasing constituents accelerate the rate of oxidation. Exner plot confirms the operation of same mechanism in all the sulfoxides studied. Electrophilic addition of Br+ to sulfur atom results in an electron-deficient sulfonium centre which decomposes in a slow rate-limiting step. The rate coefficients are treated in terms of multiparametric extensions of the Hammett equation to have more insight into the mechanistic aspects.
- Meenakshisundaram, Subbiah,Amutha
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p. 679 - 682
(2008/09/18)
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- Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid
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A highly efficient and selective oxidation of sulfides to sulfones with periodic acid catalyzed by CrO3 is described. A variety of electron-rich and electron-deficient sulfides were oxidized to sulfones with 2 mol% CrO3 in acetonitrile at room temperature in excellent yields. Sulfides with other readily oxidized functional groups were selectively oxidized to sulfones in high yields with 10 mol% CrO3 in ethyl acetate/acetonitrile at -35 °C.
- Xu, Liang,Cheng, Jie,Trudell, Mark L.
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p. 5388 - 5391
(2007/10/03)
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- Convenient one-pot procedure for converting aryl sulfides to nitroaryl sulfones
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When treated with nitrogen dioxide and ozone in inert solvent at 0°C or below, aryl sulfides underwent smooth oxidative nitration to give nitroaryl sulfones in good yield. Using this methodology, a series of mono- and di-nitrated aryl sulfones were prepared from methyl phenyl sulfide and diphenyl sulfide and their physical data are presented.
- Nose, Masatoshi,Suzuki, Hitomi
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p. 1065 - 1071
(2007/10/03)
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- Polymer electrolyte and process for producing the same
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A polymer electrolyte having, in a main chain, a structural unit represented by the following formula (1):-[Ar1-(SO2-N-(X+)-SO2-Ar2)m-SO2-N-(X+)-SO2-Ar1-O]- wherein Ar1 and Ar2 independently represent a divalent aromatic groups, m represents an integer of 0 to 3, and X+ represents an ion selected from hydrogen ion, an alkali metal ion and ammonium ion, which is excellent in proton conductivity, thermal resistance and strength. The polymer electrolyte is soluble in solvents and has excellent film forming property and recycling efficiency.
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- Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions
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Aromatic and aliphatic sulfides are oxidized to sulfoxides or sulfones in high yield with 30% hydrogen peroxide under organic solvent- and halogen-free conditions. Dialkyl and alkyl aryl sulfides are cleanly oxidized to sulfoxides using aqueous hydrogen peroxide without catalysts. The best catalyst for the sulfone synthesis consists of sodium tungstate, phenylphosphonic acid, and methyltrioctylammonium hydrogensulfate. Co-existing primary or secondary alcohol or olefinic moieties are unaffected under such conditions.
- Sato, Kazuhiko,Hyodo, Mamoru,Aoki, Masao,Zheng, Xiao-Qi,Noyori, Ryoji
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p. 2469 - 2476
(2007/10/03)
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- Mechanism of oxygenation of aryl methyl and diaryl sulphoxides by peroxomonophosphoric acid
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The kinetics of oxygenation of the title sulphoxides by peroxomonophosphoric acid in aqueous acetic acid follows an overall second-order kinetics, first-order in each reactant. An analysis of the influence of [H+] reveals that H3PO5 is the active species in the oxidation. The structure - reactivity studies with different substituents on the phenyl ring give evidence for the formation of an electron deficient sulphonium ion intermediate as the correlation between log k2 and σ gives a negative ρ value (ρ=-0.47±0.09, r=0.988, s=0.03 at 35°C for aryl methyl sulphoxides and ρ=-0.54±0.11, r=0.983, s=0.07 at 35°C for diaryl sulphoxides). It is proposed that the mechanism involves the nucleophilic attack of the sulphoxide sulphur on the peroxo-oxygen of H3PO5 in the rate-limiting step.
- Suthakaran,Rajagopal,Srinivasan
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p. 1369 - 1374
(2007/10/03)
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- Catalysis of the oxone oxidation of some sulphoxides by Ru(III)
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The kinetics of oxidation of some sulphoxides with oxone in the presence of Ru(III) has been described. The catalytic activity of Ru(III) has been demonstrated with several diaryl, dialkyl and alkyl aryl sulphoxides, all of which are found to undergo oxidation under homogenous conditions. Homolytic fission of the peroxide bond is ruled out. The reaction exhibits first-order dependence on the concentration of Ru(III) is observed. Reactions have small substituent effects with ρ = -0.3. The rates increase substantially with increasing water content in aqueous acetic acid. The rate data are consistent with the mechanism involving electron transfer from electrophilic perhydroxyl oxygen of oxone to sulphoxide. The rate coefficients are treated in terms of multiparameter extensions of the Hammett equation to have more insight into the mechanistic aspects.
- Meenakshisundaram, Subbiah,Sathiyendiran, V.
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p. 1118 - 1133
(2007/10/03)
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- An efficient method for the oxidation of organic sulfides to sulfones
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Mild and safe oxidation of dialkyl-, diaryl- and alkyl-aryl sulfides (1a-m) to the corresponding sulfones (2a-m)by using urea-hydrogen peroxide/formic acid system is reported. Wiley-VCH Verlag GmbH, 1999.
- Balicki, Roman
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p. 184 - 185
(2007/10/03)
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- A mild and efficient procedure for the oxidation of organic sulfides to sulfones by use of urea-hydrogen peroxide/trifluoroacetic anhydride system
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Selective, mild and safe oxidation of dialkyl-, diaryl- and alkyl-aryl sulfides to the corresponding sulfones was achieved by using of urea- H2O2/trifluoroacetic anhydride system.
- Balicki, Roman
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p. 2235 - 2239
(2007/10/03)
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- Oxidation of sulfides with H2O2 catalyzed by Na2WO4 under phase-transfer conditions
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A simple and efficient method was developed for the synthesis of selected dialkyl, alkylaryl and diaryl sulfones via oxidizing respective sulfides with hydrogen peroxide in the two-phase, water-dichlorocthane system in the presence of Na2WO4 and [Bu4N]Cl.
- Stec,Zawadiak,Skibinski,Pastuch
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p. 1121 - 1123
(2007/10/03)
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- Fluorodenitration of activated diphenyl sulphones using tetramethylammonium fluoride
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Fluorodenitration of nitro-substituted diphenyl sulphones occurs readily in dipolar aprotic solvents using tetramethylammonium fluoride as the source of fluoride, although other reactions including fluorodesulphonylation can sometimes occur in competition. - Keywords: Fluorodenitration; Diphenyl sulphones; Tetramethylammonium fluoride; NMR spectroscopy; Mass spectrometry
- Clark, James H.,Wails, David
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p. 201 - 206
(2007/10/02)
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- Oxidation of some Disubstituted Diphenyl Sulphoxides with Sodium N-Bromobenzene Sulphonamide in Presence of Mercury(II). A Kinetic and Mechanistic Study
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Kinetics of bromamine-B (BAB) oxidation of some p- and p'-disubstituted sulphoxides, to give the corresponding sulphones, have been studied in aqueous acetic acid medium.A first order dependence on the concentration of each reactant was observed.Rate data showed an inverse dependence on and a fractional order in +>.The reactions are little affected by the addition of HgII, ruling out the catalytic role.A negative ρ value suggests the sulphur becoming electron-dificient in the transition state.The rate-limiting step involves the interaction of the substrate and +> species.
- Mangalam, G.,Sundaram, Subbiah Meenakshi
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p. 819 - 821
(2007/10/02)
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- Kinetics and mechanism of oxidation of dimethyl, methyl phenyl and diaryl sulphoxides by N-bromocaprolactam
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The oxidation of dimethyl (DMSO) and methyl phenyl (MPSO) sulphoxides by N-bromocaprolactam (NBC) follows zero order kinetics in , but that of diphenyl sulphoxide (DPSO) is first order in .HClO4 accelerates the rate of all the oxidation reactions.However, added caprolactam retards the oxidation of only DPSO.
- Srinivasan, C.,Jegatheesan, P. Pandarakutty
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p. 250 - 252
(2007/10/02)
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- Substituent effects in cooxidation: Cr(VI) - oxalic acid - sulfoxides systems
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The kinetics of cooxidation of several substituted phenyl methyl sulfoxides and oxalic acid with Cr(VI) have been carried out in the presence of perchloric acid.The reaction is first order each in sulfoxide, oxalic acid, Cr(VI), and H1+.The products of oxidation are sulfones and carbon dioxide.Electron-releasing groups in the phenyl ring accelerate the rate while electron-withdrawing groups retard it.The Hammett correlation yields a reaction constant of -0.927 +/- 0.08 (r = 0.994) at 313 K.Addition of aluminum nitrate prevents the occurence of cooxidation.Based on the kinetic information a suitable mechanism has been proposed.Diaryl sulfoxides behave in an analogous manner in the cooxidation.
- Srinivasan, C.,Jegatheesan, P. Pandarakutty,Rajagopal, S.,Arumugam, N.
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p. 2421 - 2424
(2007/10/02)
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- Mechanism of Oxidation of Aryl Methyl Sulphoxides and Diaryl Sulphoxides by Potassium Bromate
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The oxidation of aryl methyl and diaryl sulphoxides in aqueous acetic acid at constant and ionic strength is first order each in and .An excellent correlation exists between logk2 and the Hammett ? constants (ρ=-2.05, r=0.997, s=0.05, confidence limit on ρ=+/-0.10 in 50percent aq acetic acid (v/v) at 35 deg for aryl methyl sulphoxides and ρ=-1.82, r=0.992, s=0.12, confidence limit on ρ=+/-0.32 in 75percent aq acetic acid (v/v) at 35 deg for diaryl sulphoxides).The high negative ρ-value in the two series indicates considerable charge development in the transition state.
- Srinivasan, C.,Jegatheesan, P. Pandarakutty,Arumugam, N.
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p. 678 - 680
(2007/10/02)
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- Use of Potassium Bromate. Oxidation of Organic Sulphur Compounds
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Oxidation of various organic sulphur compounds by potassium bromate under different experimental conditions was studied.
- Adak, Mohini Mohan,Banerjee, Gopal Chandra,Banerjee, Amalendu
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p. 224 - 228
(2007/10/02)
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