- Kinetic Modelling of the catalytic oxidation of 2-(methylmercapto)-benzothiazole under mild conditions
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2-(Methylmercapto)-benzothiazole oxidation was performed over Copper modified zeolites. The microporous materials were synthesized by the hydrothermal crystallization method and later modified with metal incorporation by wet impregnation. The solid cataly
- Córdoba,Saux,Pierella
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Read Online
- Transition metal-modified polyoxometalates supported on carbon as catalyst in 2-(methylthio)-benzothiazole sulfoxidation
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Polyoxometalates with lacunary Keggin structure modified with transition metal ions [PW11O39 M(H2O)]5-, where M = Ni2+, Co2+, Cu2+ or Zn2+, were synthesized and supported on activated carbon to obtain the PW11MC catalysts. Using FT-IR and DTA-TGA it was concluded that the [PW11O39M(H2O)]5- species are interacting with the functional groups of the support, and that thermal treatment leads to the loss of the coordinatively bonded water molecules without any noticeable anion degradation. The activity and selectivity of the catalysts in the sulfoxidation reaction of 2-(methylthio)-benzothiazole, an emerging environmental pollutant, were evaluated. The reaction was carried out in acetonitrile as solvent using H2O2 35% p/v as a clean oxidant. The conversion values decreased in the following order: PW11NiC > PW11CuC > PW11CoC > PW11ZnC, with selectivity to sulfoxide higher than 69%. The catalyst could be reused without appreciable loss of the catalytic activity at least three times. The materials were found to be efficient and recyclable catalysts for 2-(methylthio)-benzothiazole sulfoxidation in order to obtain a more biodegradable product than the corresponding substrate. [Figure not available: see fulltext.]
- Frenzel, Romina A.,Romanelli, Gustavo P.,Blanco, Mirta N.,Pizzio, Luis R.
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- Active potassium niobates and titanoniobates as catalysts for organic sulfide remediation
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Pure (KNbO3) and titanium-substituted (KTi0.1Nb0.9O3 and KTi0.2Nb0.8O3) potassium niobates with perovskite crystalline structures were prepared, characterized and tested as catal
- Saux, Clara,Leal Marchena, Candelaria,Dinamarca, Robinson,Pecchi, Gina,Pierella, Liliana
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- Selective and mild sulfoxidation of 2-sulfylbenzothiazole using hydroperoxides derived from cyclohexanone in the absence of catalyst
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Alkyl hydroperoxides derived from cyclohexanone are attractive oxidants because they are easily available, more reactive than TBHP but much less acidic than m-CPBA. Wherein 1,1′-peroxybis(1-hydroperoxycyclohexane) (C) can be generated by the current simply method and displays the excellent reactivity and selectivity based on oxidative reactions of various benzothiazolyl sulfides substituted by different function groups. The research found that the reactions can be performed in the absence of catalyst and under very mild conditions optimized. Yields of sulfoxides is higher than 90%, no or a little reaction happened at the proximal double bond、 N and S atoms in the benzothiazolyl moiety. Phenyl sulfide as the substrates was also examined for the reaction scope test. The results show that they were uniquely and completely oxidized to sulfoxides in 1 h. A mild, environmentally friendly, catalyst-free aryl sulfide sulfoxidation method has been developed.
- Shi, Wenjun,Yu, Chunmian,Zhou, Xinrui,Zhu, Shihao
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- Synthesis method of sulfoxide compound
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The invention discloses a method for preparing sulfoxide derivatives with industrial application value through substituted diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfide compounds. Under electrochemical reaction conditions, diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfide compounds which are wide in source and easy to prepare and have structural diversity are used as raw materials, lithium perchlorate (LiClO4) is used as an electrolyte, acetonitrile (CH3CN) is used as a solvent, and oxygen is used as an oxidizing agent to prepare the diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfoxide derivatives. Compared with reported preparation methods of sulfoxide derivatives, the preparation method disclosed by the invention is green, environment-friendly, safe, energy-saving, wide in substrate application range, good in compatibility of product functional groups, easy in obtaining of raw materials and simple and convenient to operate.
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Paragraph 0031-0033; 0107-0109
(2021/04/07)
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- Electrochemical Scalable Sulfoxidation of Sulfides with Molecular Oxygen and Water
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An efficient and chemoselective synthesis of sulfoxides through the electrooxidation of sulfides has been well developed. This protocol takes advantage of electricity as the terminal oxidant and of molecular oxygen and water as the oxygen atom sources. A variety of structurally diverse sulfoxide compounds are assembled in moderate to excellent yields. The scaled-up reactions at 6–20 mmol show the good practicability and application potential of this methodology. A possible free radical mechanism has been proposed to rationalize the reaction procedure.
- Cheng, Zhen,Gao, Xinglian,Yao, Lingling,Wei, Zhaoxin,Qin, Guohui,Zhang, Yonghong,Wang, Bin,Xia, Yu,Abdukader, Ablimit,Xue, Fei,Jin, Weiwei,Liu, Chenjiang
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p. 3743 - 3747
(2021/07/26)
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- Highly Chemoselective and Enantioselective Catalytic Oxidation of Heteroaromatic Sulfides via High-Valent Manganese(IV)-Oxo Cation Radical Oxidizing Intermediates
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A manganese complex with a porphyrin-like ligand that catalyzes the highly chemoselective and enantioselective oxidation of heteroaromatic sulfides, including imidazole, benzimidazole, indole, pyridine, pyrimidine, pyrazine, sym-triazine, thiophene, thiaz
- Dai, Wen,Shang, Sensen,Lv, Ying,Li, Guosong,Li, Chunsen,Gao, Shuang
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p. 4890 - 4895
(2017/07/24)
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- Carbon-supported metal-modified lacunary tungstosilicic polyoxometallates used as catalysts in the selective oxidation of sulfides
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Lacunary tungstosilicic polyoxometallates modified with transition metal ions [SiW11O39M(H2O)]6-, where M = Mn2+, Fe2+, Co2+or Cu2+, were synthesized and supported on activated carbon to obtain the SiW11MC catalysts. The samples were characterized by FT-IR, XRD, N2 adsorption-desorption measurements, and the acidic properties were determined using the isopropanol dehydration test reaction. The activity and selectivity of the catalysts were evaluated in the selective oxidation of a series of sulfides to sulfoxides or sulfone. The reaction was carried out in acetonitrile as solvent using H2O2 35% p/V as a clean oxidant. The conversion values decreased in the following order: SiW11MnC > SiW11FeC > SiW11CuC > SiW11CoC. The catalysts were reused without appreciable loss of their catalytic activity. It was found that the activity of the catalysts decreases in parallel with the increment in the reduction temperature values. The most easily reducible catalyst displayed the highest conversion values. We found a convenient and selective procedure for oxidizing sulfides to sulfoxides or sulfones using aqueous hydrogen peroxide and a catalytic amount of lacunary tungstosilicic polyoxometallates supported on carbon at low temperatures (20-50 °C) in a reasonably short reaction time
- Frenzel, Romina,Sathicq, ángel G.,Blanco, Mirta N.,Romanelli, Gustavo P.,Pizzio, Luis R.
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- Carbonyl olefination of diaryl ketones with heteroaryl sulfoxides
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Heteroaryl sulfones are capable of converting the carbonyl functionalities to alkenyl motifs, which is well-known as Julia-Kocienski olefination reaction. However, their sulfoxide analogues have failed in such an olefination reaction for over twenty years
- Gao, Bing,Hu, Jingyu,Zhao, Yanchuan,Hu, Jinbo
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supporting information
p. 4180 - 4183
(2015/06/22)
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- Selective Oxidation of Sulfides to Sulfoxides Using Modified Keggin Heteropolyacids as Catalyst
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The use of modified Keggin phosphomolybdic heteropolyacids (HPA) (V and Al) as catalysts in the selective oxidation of sulfides to the corresponding sulfoxides is reported. Excellent yields were obtained (13 examples: 79%-95%), using 35% (w/v) aqueous hydrogen peroxide as oxidant, and acetonitrile as solvent at 25°C. The relationship between the electron densities of the sulfur atoms, which was estimated by molecular theoretical calculations, and the oxidative relativities of the sulfur-containing compounds was also investigated. The results indicate that the time for 100% conversion decreases with an increase in electron density.
- Palermo, Valeria,Sathicq, Angel G.,Vazquez, Patricia G.,Romanelli, Gustavo P.
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supporting information
p. 1423 - 1432
(2015/10/29)
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- A general and selective zinc-catalyzed oxidation of sulfides to sulfoxides
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A general zinc-catalyzed oxidation of sulfides to sulfoxides has been developed. All the reactions proceeded at room temperature. Hydrogen peroxide was used as a green oxidant. Twenty-one examples of sulfoxides were prepared in moderate to excellent yields.
- Wu, Xiao-Feng
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experimental part
p. 4328 - 4331
(2012/09/22)
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- Practical synthesis of β-acyl and β-alkoxycarbonyl heterocyclic sulfones
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A short and efficient synthesis for β-acyl and β-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocyclic core is presented here. The method seems to be general and provides the desired C-nucleophiles in very good to excellent yields from readily available starting materials.
- Pospisil, Jiri,Sato, Hitoshi
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p. 2269 - 2272
(2011/06/11)
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- Keggin heteropolycompounds as catalysts for liquid-phase oxidation of sulfides to sulfoxides/sulfones by hydrogen peroxide
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H4PMo11VO40, H5PMo 10V2O40 and H9PMo6V 6O40 acids and an acidic pyridinium salt of H 4PMo11VO40 were synthesized. They were characterized by FT-IR and the variations of their acid properties were determined by titration with n-butylamine. They proved to be highly active and selective catalysts for the hydrogen peroxide oxidation of methyl phenyl sulfide to the corresponding sulfoxide or sulfone. The conversion and selectivity results may be explained in terms of the co-existence of acidic and oxidative properties in the catalysts. On the other hand, a convenient catalytic homogeneous procedure has been found to oxidize different sulfides to sulfoxides or sulfones, with 35% aqueous H2O2, using (PyH)H 3PMo11VO40 as catalyst. The oxidation reaction is carried out at room temperature for sulfoxides or 40 °C for sulfones and requires a short time. The sulfoxides or sulfones were obtained with excellent yields by controlling the amount of H2O2.
- Romanelli, Gustavo P.,Villabrille, Paula I.,Cáceres, Cármen V.,Vázquez, Patricia G.,Tundo, Pietro
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p. 726 - 730
(2013/01/09)
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- Electro- and acid-catalysis in tetrafluoroborate-based ionic liquid: new alternative routes for the oxidation of sulfides with UHP
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By means of anodic activation, BF4-based ionic liquid was found to play the triple role of electrolysis/reaction medium, supporting electrolyte and pre-catalyst versus the oxidation of sulfides with UHP. Galvanostatic electrolysis in the presence of substrate and UHP molecules allowed the fast, efficient and selective achievement of sulfoxides. Comparable results have been attained by acid catalysis based on R-CSA.
- Palombi, Laura,Bocchino, Carmen,Caruso, Tonino,Villano, Rosaria,Scettri, Arrigo
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p. 5611 - 5613
(2008/12/22)
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- Comparative study of metal-catalyzed iminations of sulfoxides and sulfides
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A comparative study of the imination of sulfur compounds with various metal catalysts in combination with isolated or in situ generated iminoiodinanes (PhI=NR) as nitrogen sources is presented. The influence of the metal catalyst towards the imination of a variety of substituted sulfoxides has been evaluated. Moreover, the effect of the different oxidation states of sulfur on the reactivity and selectivity of the nitrogen transfer redox process in the formation of sulfilimines and sulfoximines was studied. Depending on both the specific metal catalyst as well as the employed nitrene precursor, the sulfide/sulfoxide imination ratio varied in transformations of thianthrene-5-oxide and substituted para-thio phenylsulfoxides.
- Mancheno, Olga Garcia,Bolm, Carsten
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p. 6674 - 6681
(2008/03/15)
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- Oxidation of allylic alcohols, amines, and sulfides mediated by assembled triphase catalyst of phosphotungstate and non-cross-linked amphiphilic copolymer
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A novel catalyst PWAA, an assembled complex of phosphotungstic acid (H 3PW12O40) and a non-cross-linked copolymer of N-isopropylacrylamide with an ammonium, was developed. It is an amphiphilic, cross-linked, and supramolecular insoluble complex and showed catalytic activity on oxidation with aqueous hydrogen peroxide. PWAA, used in 2.7×10 -5-2.0×10-3molequiv., catalyzed oxidation of allylic alcohols, amines, and sulfides efficiently. The turnover number (TON) of PWAA reached up to 35,000. PWAA showed a good stability in organic/aqueous media and was reused three to five times.
- Yamada, Yoichi M.A.,Tabata, Hidetsugu,Ichinohe, Masato,Takahashi, Hideyo,Ikegami, Shiro
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p. 4087 - 4096
(2007/10/03)
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- Oxidation of amines and sulfides catalyzed by an assembled complex of phosphotungstate and non-cross-linked amphiphilic polymer
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Oxidation of sulfides and amines was performed with an assembled catalyst of phosphotungstate and non-cross-linked amphiphilic polymer. The reactions proceeded with hydrogen peroxide under organic solvent-free conditions. This insoluble catalyst was reused five times with the turnover number up to 500.
- Yamada, Yoichi M. A.,Tabata, Hidetsugu,Takahashi, Hideyo,Ikegami, Shiro
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p. 2031 - 2034
(2007/10/03)
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- Convenient synthesis of 2-(thiocyanomethylthio)benzothiazole
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A highly efficient and general route has been developed for 2-(thiocyanomethylthio)benzothiazole 3 which is synthesised by reacting a chlorinating agent with 2-mercaptobenzothiazole 1 followed by reactions involving 2-(methylthio)benzothiazole 1b and 2-(methylsulfinyl)benzothiazole 2 under various conditions.
- Muthusubramanian, Lakshmi,Mitra, Rajat B.,Sundara Rao,Raghavan
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p. 1331 - 1334
(2007/10/03)
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- Phenyltrimethylammonium Tribromide for Selective Oxidation of Sulfides to Sulfoxides. A Convenient Synthesis of Sulfinyl-18O-Labelled Sulfoxide Carboxylic Acids
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Various sulfides can be oxidized selectively to the corresponding sulfoxides in high yields using phenyltrimethylammonium tribromide in aqueous pyridine solution.This method allows 18O-labelled sulfoxides to be prepared with no loss of isotope
- Rabai, Jozsef,Kapovits, Istvan,Tanacs, Bela,Tamas, Jozsef
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p. 847 - 849
(2007/10/02)
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- Generation of Sulfenate Salts via Ipso-substitution of Azaheterocyclic Sulfoxides. First Preparation and Characterization of Sodium 2-Pyridinesulfenate
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2-Alkyl- or 2-aryl-sulfinylpyridine N-oxides undergo ipsosubstitution reaction with sodium ethoxide to afford sodium sulfenates which were converted soon to the corresponding sulfinates upon contact with oxygen.Sodium 2-pyridinesulfenate was prepared and characterized by FT-IR as the first example of stable sulfenate.
- Furukawa, Naomichi,Konno, Yasuo,Tsuruoka, Masayuki,Fujihara, Hisashi,Ogawa, Satoshi
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p. 1501 - 1504
(2007/10/02)
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- Preparation of 2-(isopropylsulfinyl)benzothiazole
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There is disclosed a novel class of vulcanization accelerators, specifically compounds such as 2-(isopropylsulfinyl)-benzothiazole.
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