127-63-9Relevant articles and documents
Diruthenium(II,III) tetramidates as a new class of oxygenation catalysts
Villalobos, Leslie,Cao, Zhi,Fanwick, Phillip E.,Ren, Tong
, p. 644 - 650 (2012)
Two new diruthenium(II,III) tetramidate compounds, Ru 2(NHOCC(CH3)2)4Cl (1) and Ru 2(NHOCCH2CH3)4Cl (2) have been prepared and structurally characterized by X-ray crys
A novel method for the synthesis of aryl sulfones
Steensma, Ruo W.,Galabi, Sharen,Tagat, Jayaram R.,McCombie, Stuart W.
, p. 2281 - 2283 (2001)
New sulfones were produced from aryl trifluoromethyl sulfones and Grignard reagents in good to high yields. The advantage of this transformation over a previous method by which sulfones were prepared from sulfonyl fluorides and organometallic reagents is discussed.
Metal Catalysis in Oxidation by Peroxides. 30. Electrophilic Oxygen Transfer from Anionic, Coordinatively Saturated Molybdenum Peroxo Complexes
Campestrini, S.,Conte, V.,Furia, F. Di,Modena, G.,Bortolini, O.
, p. 5721 - 5724 (1988)
Two anionic and coordinatively saturated oxodiperoxomolybdenum complexes, -Bu4N+ (L=C5H4NCO2- or C5H4N(O)CO2-), have been used as oxidants for a series of organic sulfides and sulfoxides in DCE.Quantitative yields of sulfoxides and sulfones, respectively, have been obtained.Spectroscopic (1H and 13C NMR) and kinetic evidence rule out any coordination process between the substrate and the oxidant requiring the formation of an unsaturated site on the metal.The data collected point to an oxidation mechanism involving a bimolecular reaction.This, at least for sulfide oxidation, appears to proceed through an electrophilic oxygen transfer from the peroxo complex to the substrate.
Oxidation of sulfides with a silica-supported peracid in supercritical carbon dioxide under flow conditions: Tuning chemoselectivity with pressure
Mello, Rossella,Olmos, Andrea,Alcalde-Aragones, Ana,Diaz-Rodriguez, Alba,Gonzalez Nunez, Maria Elena,Asensio, Gregorio
, p. 6200 - 6206 (2010)
Supercritical carbon dioxide is a convenient medium for performing the selective oxidation of sulfides 1 to either sulfoxides 2 or sulfones 3 with [2-percarboxyethyl]-functionalized silica (4) under flow conditions. The chemoselectivity of the reaction, which results from the different diffusion rates of sulfide and sulfoxide over the reagent bed, can be controlled by adjusting the pressure and the hydration of the silica surface as both the solvating power of the mobile phase and the surface activity of the stationary phase determine the migration rates of sulfide 1 and sulfoxide 2 over the supported peroxide. The results elucidate the impact of surface phenomena on the course of chemical reactions carried out under flow conditions. The oxidation of sulfides 1 with hydrated [2-percarboxyethyl]-functionalized silica (4) in scCO2 under flow conditions can be tuned to give either sulfoxides 2 or sulfones 3 by adjusting the pressure.
Selectivity in Oxidation of Sulfides with Hydrogen Peroxide by +(CH2)15CH3>PM12O403- and +(CH2)15CH3>34>3- (M=Mo or W)
Ishii, Yasutaka,Tanaka, Hiroyuki,Nishiyama, Yutaka
, p. 1 - 4 (1994)
Dramatical difference in selectivity was observed in the hydrogen peroxide oxidation of sulfides by +(CH2)15CH3>3PW12O403- (CWP) and +(CH2)15CH3>34>3- (PCWP) under the two-phase sy
Harvey,Stegeman
, (1924)
New niobium heteropolyacid included in a silica/alumina matrix: Application in selective sulfoxidation
Colombo Migliorero, María B.,Palermo, Valeria,Romanelli, Gustavo P.,Vázquez, Patricia G.
, p. 89 - 97 (2021)
A new heteropolyacid, derived from phosphomolybdic acid containing niobium (PNbMo), was synthesized and included in silica, alumina, and silica/alumina matrixes by sol-gel technique, in order to use it as heterogeneous catalyst. The matrixes confer stability to the active phase, good textural and morphological properties. PNbMo and included materials were characterized by 31P-NMR, FT-IR, UV–vis, TGA, SEM, TEM, XRD, N2 physisorption, and potentiometric titration, and tested as catalyst in the sulfoxidation of diphenyl sulfide under suitable conditions. The redox activity was compared with phospomolybdic acid and correlated with the edge energy obtained from UV–vis absorption spectra. The best results in diphenyl sulfide sulfoxidation were obtained with PNbMo-SiAl-4:1 (92% conversion and 95% selectivity at 3 h) and with PNbMo-Si (92% conversion and 94% selectivity at 4 h). The reuse of these catalysts was evaluated.
Kikukawa et al.
, p. 831 (1969)
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Oae et al.
, p. 543,544 (1965)
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Reactions on solid supports: Oxidation of sulfides to sulfoxides catalyzed by metalloporphyrins supported on silicagel
Pautet,Daudon
, p. 1457 - 1458 (1991)
The use of metalloporphyrins immobilized on silica, with iodosylbenzene as oxidant, leads to a selective oxidation of sulfides to sulfoxides.
Rapid oxidation of sulfides and sulfoxides with sodium hypochlorite
Khurana, Jitender M.,Panda, Atulya K.,Ray, Abhijit,Gogia, Amita
, p. 234 - 237 (1996)
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Heteropolymetallic complexes containing ReO4-: Catalytic oxidation of sulfide
Li, Chen,Peng, Xiao,Zhang, Shou-Chun,Chai, Li-Yuan,Yi, Xiao-Yi
, p. 113 - 116 (2013)
Heteropolymetallic complexes [(salen)Ti(ReO4)2] (1) and [{(salen)Ti(ReO4)}2(μ-O)] (2) are easily obtained in high yields via reaction of [(salen)TiCl2] and [{(salen)TiCl 2}2(μ-O)] with (Me3SiO)ReO3, respectively (where, salen = (S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene) cyclohexane-1,2-diamine dianion). The structure of complex 2 was established by single-crystal X-ray diffraction. The tetrahedral geometry of the ReO 4- anion links the dititanium unit of {(salen)Ti} 2(μ-O) in the axial positions. The Re-O-Ti bridge angles range from 146.1(2) to 162.6(2) with a Re?Ti separation of 3.780 A?. Complexes 1 and 2 are capable of catalytic oxidation of sulfides with tBuOOH.
An improved high yielding immobilization of vanadium Schiff base complexes on mesoporous silica via azide-alkyne cycloaddition for the oxidation of sulfides
Jain, Suman L.,Rana, Bharat S.,Singh, Bhawan,Sinha, Anil K.,Bhaumik, Asim,Nandi, Mahasweta,Sain, Bir
, p. 374 - 377 (2010)
Azide-alkyne [3+2] cycloaddition "click reaction" was found to be a simple yet improved approach for the efficient immobilization of oxo-vanadium(iv) tridentate Schiff base complexes to mesoporous silica via covalent attachment as it occurred under mild reaction conditions and provided high catalyst loading compared to the direct immobilization of oxo-vanadium(iv) tridentate Schiff base complex to 3-chloropropylsilyl functionalized silica support.
Fe-pillared bentonite-an efficient catalyst for sulfonylation of arenes using aryl and alkyl sulfonyl chlorides
Singh, Devendrapratap U.,Singh, Pankajkumar R.,Samant, Shriniwas D.
, p. 9079 - 9082 (2004)
Fe-pillared bentonite (Fe-PILC) was shown to be an extremely efficient catalyst for the sulfonylation of activated as well as unactivated carbocyclic aromatic compounds and heterocyclic aromatic compounds. The catalyst was also found to be recyclable.
Evidence for a higher oxidation state of manganese in the reaction of dinuclear manganese complexes with oxidants. Comparison with iron based gif chemistry
Barton, Derek H.R.,Choi, Seung-Yong,Hu, Bin,Smith, Jason A.
, p. 3367 - 3378 (1998)
Binuclear manganese complexes mimic the catalase enzyme by converting hydrogen peroxide rapidly and efficiently to oxygen and water. The complex (1) may he activated by either periodic acid or Oxone and can oxidize selected organic substrates. Potassium manganate gave similar oxidation products suggesting that the manganese is transformed to a higher oxidation state. Kinetic studies with the Mn(IV)-Mn(IV) complex show an induction period indicating that it is not the active catalyst. Further studies suggested that the actual catalytic species is a Mn(III)-Mn(IV) complex. These complexes show similar properties to the activation of FeCl3 with hydrogen peroxide. This is particularly evident by the formation of a new and unusual peroxide from argosterol acetate.
Effect of Organic Solvents on the Rate of Oxidation of Sulfoxides with Peroxy Acids
Dutka, V. S.,Dutka, Yu. V.,Midyana, G. G.,Pal’chikova, E. Ya.
, p. 329 - 334 (2020)
Abstract: The reaction of sulfoxides with peroxy acids in various organic media was studied. The reaction mechanism involves the rapid formation of a sulfoxide-–peroxy acid intermediate which decomposes in the second stage to form carboxylic acid and the corresponding sulfone. The second stage is the rate-limiting step. The reaction medium significantly affects the rate of oxidation. The calculated activation parameters of the oxidation process indicate a compensation effect in the investigated reaction. Correlations between the main physicochemical parameters of solvents and the effective rate constants (k) of dimethyl sulfoxide oxidation with peroxy acids were found. Depending on the reaction conditions, the main factors affecting the k values are specific and nonspecific solvation of the reactants and structural factors.
Sandwich type polyoxometalates encapsulated into the mesoporous material: Synthesis, characterization and catalytic application in the selective oxidation of sulfides
Naseri, Elham,Khoshnavazi, Roushan
, p. 28249 - 28260 (2018)
The A-type sandwich polyoxometalates of [(HOSnIVOH)3(PW9O34)2]12- (P2W18Sn3) and [(OCeIVO)3(PW9O34)2]12- (P2W18Ce3) were immobilized for the first time into the porous metal-organic framework MIL-101(Cr). FT-IR, powder X-ray diffraction, SEM-EDX, ICP analysis, N2 adsorption and thermogravimetric analysis collectively confirmed immobilization and good distribution of polyoxometalates into cages of MIL-101(Cr). The catalytic activities of the homogeneous P2W18Sn3 and P2W18Ce3 and the corresponding heterogeneous catalysts were examined in the oxidation of sulfides to sulfones with H2O2 as the oxidant at room temperature. The effects of different dosages of polyoxometalates, type of solvent, reaction time, amount of catalyst and oxidant in this catalytic system were investigated. The new P2W18Sn3@MIL-101 and P2W18Ce3@MIL-101 nanocomposites exhibited good recyclability and reusability in at least five consecutive reaction cycles without significant loss of activity or selectivity.
Fe(III) exchanged montmorillonite: A mild and ecofriendly catalyst for sulfonylation of aromatics
Choudary,Chowdari, N. Sreenivasa,Kantam, M. Lakshmi,Kannan
, p. 2859 - 2862 (1999)
Fe(III) exchanged montmorillonite clay catalyses Friedel-Crafts sulfonylation of arenes with arylsulfonyl chlorides to obtain the corresponding sulfones in excellent yields.
Selective oxidation of sulfides to sulfoxides with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) in the presence of alcohols
Iwahama, Takahiro,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 9059 - 9062 (1998)
Aerobic oxidation of various sulfides using N-hydroxyphthalimide (NHPI) in the presence of alcohols was examined. For instance, the oxidation of diphenyl sulfide in the presence of cyclohexanol and a catalytic amount of NHPI in benzonitrile gave diphenyl
Preparation and reactivities of novel (diacetoxyiodo)arenes bearing heteroaromatics
Togo,Nabana,Yamaguchi
, p. 8391 - 8394 (2000)
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PHENYLATION OF SULFUR DIOXIDE BY PENTAPHENYLBISMUTH
Sharutin, V. V.,Ermoshkin, A. E.
, p. 2414 (1987)
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Factors affecting the reactivity and selectivity in the oxidation of sulfides with tetra-n-butylammonium peroxomonosulfate catalyzed by Mn(III) porphyrins: Significant nitrogen donor effects
Rezaeifard, Abdolreza,Jafarpour, Maasoumeh,Raissi, Heidar,Ghiamati, Ebrahim,Tootoonchi, Aida
, p. 592 - 598 (2011)
The oxidation of aryl sulfides by tetra-n-butylammonium peroxomonosulfate (n-Bu4NHSO5) was carried out in the presence of six different manganese (III) tetraarylporphyrins [Mn(Por)s] as biomimetic catalysts and a number of nitrogen donors as co-catalysts. There is no noticeable difference between the reactivity of sulfides, in the presence of electron-rich Mn(por)s, whereas, for electron-deficient catalysts, conversion rates are different. Nevertheless, the over-oxidation of sulfoxide is more sensitive to both the nature of substituents attached to the sulfur atom in substrates as well as porphyrin complex structure. The degree of catalytic activity of Mn(Por)s for the formation of sulfone product increases as the following order: Mn(TPFPP)OAc 2P)P]OAc 4] complex.
Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N-S Bond Activation of Sulfonamides
Zhen, Jingsong,Du, Xian,Xu, Xiaohong,Li, Yihui,Yuan, Han,Xu, Dejing,Xue, Can,Luo, Yong
, p. 1986 - 1991 (2022/02/07)
A visible-light-mediated late-stage arylation of N-S bonds in sulfonamides has been developed with using readily available imines as sulfonyl radical source. Diverse complex sulfones could be synthesized by prefunctionalizaiton and subsequent N-S bond ary
Oxovanadium and dioxomolybdenum complexes: synthesis, crystal structure, spectroscopic characterization and applications as homogeneous catalysts in sulfoxidation
Kargar, Hadi,Kaka-Naeini, Azar,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Amiri Rudbari, Hadi,Munawar, Khurram Shahzad
, p. 1563 - 1583 (2021/05/11)
New oxovanadium and dioxomolybdenum Schiff base complexes, [VO(L)(OCH3)] n and [MoO2(L)(CH3OH)], were synthesized by treating an ONO donor Schiff base (H2L) derived by condensation of 3-ethoxysalicylaldehyde and nicotinic hydrazide with oxo and dioxo acetylacetonate salts of vanadium and molybdenum (VO(acac)2 and MoO2(acac)2), respectively. The synthesized ligand and complexes were characterized by FTIR, multinuclear (1H, 13C) NMR, elemental and single crystal X-ray diffraction analysis. In both complexes, the geometry around the central metal ions was distorted octahedral as revealed by diffraction studies. Theoretical calculations of the synthesized compounds were carried out by DFT at B3LYP/Def2-TZVP level of theory, which showed good correlation with the experimental results. Moreover, the catalytic efficiency of both complexes was investigated by oxidizing aryl and alkyl sulfides in the presence of 30% H2O2 in ethanol.
