Oxidation Of Organic Sulfides Research Articles

Sodium Hypochlorite-promoted Novel Synthesis of Organic Ammonium Tribromides and Application of Phenanthroline Hydrotribromide in Chemoselective Oxidation of Organic Sulfides by Hydrogen Peroxide

Abstract A novel method of synthesis of organic ammonium tribromides (OATBs) is developed by using an inexpensive and eco-friendly sodium hypochlorite as oxidant for conversion of Br− to Br3−. The OATBs thus prepared include both quaternary ammonium tribromides and N-heterocyclic tribromides. A new addition to the family of OATBs is made in the form of phenanthroline hydrotribromide. The efficacy of this new tribromide as catalyst is ascertained in the oxidative transformation of organic sulfides to their corresponding sulfoxides and sulfones by hydrogen peroxide.

A hexanuclear manganese(ii) complex: synthesis, characterization and catalytic activity toward organic sulfide oxidation

A hexanuclear [MnII6] wheel-like assembly with naphthalene-1,8-dicarboxylate and 1,10-phenanthroline was reported. The compound acts as a catalyst toward organic sulfide oxidation.

Oxidation of Organic Sulfides by Imidazolium Fluorochromate: A Kinetic and Mechanistic Approach

Oxidation of Organic Sulfides by Imidazolium Fluorochromate: A Kinetic and Mechanistic Approach

Nanolayered manganese–calcium oxide as an efficient catalyst toward organic sulfide oxidation

We for the first time report that nanolayered Mn–Ca oxide in the presence of H2O2 is an efficient catalyst toward sulfide oxidation to sulfoxide.

Highly porous conjugated polymers for selective oxidation of organic sulfides under visible light.

High surface area porous conjugated polymers were synthesized via the high internal phase emulsion polymerization technique and micropore engineering as efficient heterogeneous photocatalysts for highly selective oxidation of organic sulfides to sulfoxides under visible light.

Extractive and Catalytic Oxidative Desulfurization of Gasoline by Methyltrioxorhenium in Ionic Liquids

For the first time, methyltrioxorhenium (MTO) is used as a catalyst for the extractive and catalytic oxidative desulfurization (ECODS) of model oil and fluid catalytic cracking (FCC) gasoline, with 30% H2O2 as the oxidant and ionic liquids as the solvent and extractant for the removal of organic sulfur at moderate temperatures (below 60 degrees C). The ECODS is highly efficient with low catalyst loading (1-5 mol %). The mono- and bisperoxorhenium compounds formed via the reactions of MTO and H2O2 are proven to be catalytic active species for the oxidation of organic sulfides, such as thioethers, thiophene, and alkyl thiophenes contained in the FCC gasoline. After the oxidation, the oxidized products were easily extracted into the ionic liquid phase from the oil phase. The sulfur removal can reach up to 99% for the model oil (with an initial sulfur content of 200 mu g/mL) and 91% of the Fushun FCC gasoline (with an initial sulfur content of ca. 142 mu g/mL) within 2 h under the optimized conditions. The octane number of the gasoline is reduced by only about 0.7, without significant changes in hydrocarbon group composition after desulfurization.

Oxidation of sulfides with hydrogen peroxide catalyzed by synthetic flavin adducts with dendritic bis(acylamino)pyridines

The catalytic activities of the cationic synthetic flavin adduct 1 with various dendritic and non-dendritic 2,6-bis(acylamino)pyridines 2 were examined for the oxidation of organic sulfides with H2O2. The adduct of 5-ethyllumiflavinium perchlorate 1a with 2b–d bearing poly(benzyl ether) dendron units acts as an efficient organocatalyst for the oxidative transformation of sulfides to the corresponding sulfoxides under mild conditions.

ChemInform Abstract: Ruthenium Nanocatalysis on Redox Reactions

AbstractReview: 388 refs.

Oxidation of Sulfides with Hydrogen Peroxide Catalyzed by Vitamin B2 Derivatives

5-Ethyl-3-methyl-2′,4′:3′,5′-di-O-methylenedioxyriboflavinium perchlorate (1, DMRFlEt+ClO4 –), derived readily from commercially available vitamin B2 (riboflavin), exhibits high catalytic activity for the oxidation of organic sulfides with hydrogen peroxide. The reaction provides an efficient and selective method for the oxidative transformation of organic sulfides to the corresponding sulfoxides under mild conditions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.]

Ruthenium Nanocatalysis on Redox Reactions

Nanoparticles have generated intense interest over the past 20 years due to their high potential applications in different areas such as catalysis, sensors, nanoscale electronics, fuel and solar cells and optoelectronics. As the large fractions of metal atoms are exposed to the surface, the use of metal nanoparticles as nanocatalysts allows mild reaction conditions and high catalytic efficiency in a large number of chemical transformations. They have emerged as sustainable heterogeneous catalysts and catalyst supports alternative to conventional materials. This review focuses on the synthesis, characterization and catalytic role of ruthenium nanoparticles (RuNPs) on the redox reactions of heteroatom containing organic compounds with the green reagent H2O2, a field that has attracted immense interest among the chemical, materials and industrial communities. We intend to present a broad overview of Ru nanocatalysts for redox reactions with an emphasis on their performance, stability and reusability. The growth in the chemistry of organic sulfoxides and N-oxides during last decade was due to their importance as synthetic intermediates for the production of a wide range of chemically and biologically active molecules. Thus design of efficient methods for the synthesis of sulfoxides and N-oxides becomes important. This review concentrates on the catalysis of RuNPs on the H2O2 oxidation of organic sulfides to sulfoxides and amines to N-oxides. The deoxygenation reactions of sulfoxides to sulfides and reduction of nitro compounds to amines are fundamental reactions in both chemistry and biology. Here, we also highlight the catalysis of metal nanoparticles on the deoxygenation of sulfoxides and sulfones and reduction of nitro compounds with particular emphasis on the mechanistic aspects.

Aerobic Oxidation of Sulfides with a Vitamin B2-Derived Organocatalyst

5-Ethyl-3-methyl-2′,4′:3′,5′-di-O-methylenedioxy-riboflavinium perchlorate (DMRFlEt+ClO4 –) is readily derived from commercially available vitamin B2 (riboflavin) and exhibits high catalytic activity for the oxidation of organic sulfides under an oxygen atmosphere (1 atm) with the assistance of hydrazine hydrate as a reductant. This is an inexpensive, convenient, and environmentally benign method for the selective oxidative transformation of sulfides into sulfoxides.

Merrifield resin supported peroxomolybdenum(vi) compounds: recoverable heterogeneous catalysts for the efficient, selective and mild oxidation of organic sulfides with H2O2

We have generated new heterogeneous catalysts by immobilizing dioxomonoperoxomolybdenum(VI) on amino acid functionalized Merrifield resin, which exhibit excellent activity, stability and selectivity for the oxidation of thioethers and dibenzothiophene (DBT) to the corresponding sulfoxides or sulfones by H2O2 at ambient temperature. The synthetic protocols are high-yielding, halogen-free, environmentally clean and safe, and operationally simple. The catalysts, [MoO2(O2)(L)2]2−-MR [L = valine (MRVMo) or alanine (MRAMo) and MR = Merrifield resin] were prepared by reacting H2MoO4 with 30% H2O2 and the respective amino acid functionalized resin, at near neutral pH. The compounds were characterized by elemental analysis, spectral studies (FTIR, Raman, 13C NMR and 95Mo NMR, diffuse reflectance UV-Vis and XPS), SEM, EDX, XRD, Brunauer–Emmett–Teller (BET) and TGA-DTG analysis. The easy recyclability of the catalysts for several catalytic cycles without change in activity and selectivity, their complete chemoselectivity towards the sulfur group of substrates bearing other oxidation prone functional groups, are important “green” attributes of these catalysts.

VO2F(dmpz)2: a new catalyst for selective oxidation of organic sulfides to sulfoxides with H2O2

A newly developed and structurally characterized vanadium complex [VO2F(dmpz)2] (dmpz=3, 5 dimethyl pyrazole) is reported as recyclable catalyst for the selective oxidation of organic sulfides with H2O2 in CH3CN at sub-ambient temperature. [VO2F(dmpz)2]–H2O2 system chemoselectively oxidizes alkyl as well as aryl sulfides in the presence of oxidation prone functional groups such as CC, –CN, and –OH. Refractory sulfides (dibenzothiophenes) are also oxidized to sulfoxides.

Hybrid Polyoxotungstates as Functional Comonomers in New Cross‐Linked Catalytic Polymers for Sustainable Oxidation with Hydrogen Peroxide

Anchoring terminal octenyl tails on molecular polyoxotungstates yield polymerizable organic-inorganic monomers with formula [{CH(2)=CH(CH(2))(6)Si}(x)O(y)SiW(w)O(z)](4-) [x = 2, w = 11, y = 1, z = 39 (1); x = 2, w = 10, y = 1, z = 36 (2); and x = 4, w = 9, y = 3, z = 34 (3)]. These molecular hybrids can use aqueous hydrogen peroxide to catalyze the selective oxidation of organic sulfides in CH(3)CN. Copolymerization of 1-3 with methyl methacrylate and ethylene glycol dimethacrylate leads to porous materials with a homogeneous distribution of the functional monomers, as indicated by converging evidence from FTIR spectroscopy and electronic microscopy. The catalytic polymers activate hydrogen peroxide for oxygen transfer, as demonstrated by the quantitative and selective oxidation of methyl p-tolyl sulfide, which was screened as model substrate. The hybrid material containing monomer 2 was also tested in n-octane to evaluate its potential for the oxidation and removal of dibenzothiophene, a well-known gasoline contaminant.

ChemInform Abstract: Catalyst‐Free Approach for Solvent‐Dependent Selective Oxidation of Organic Sulfides with Oxone.

AbstractThe oxidation of sulfides (I) with Oxone in ethanol leads to sulfoxides (II), while the oxidation in water affords sulfones (III) in high yields.

Metalloporphyrin-Catalyzed Chemoselective Oxidation of Sulfides with Polyvinylpyrrolidone-Supported Hydrogen Peroxide: Simple Catalytic System for Selective Oxidation of Sulfides to Sulfoxides

Room temperature oxidation of organic sulfides with polyvinylpyrrolidone-supported hydrogen peroxide (PVP-) in the presence of Mn(III) complexes of meso-tetraphenylporphyrin, Mn(TPP)X (X = OCN, SCN, OAc, Cl) and imidazole (ImH) leads to the highly chemoselective (ca. 90%) oxidation of sulfides to the corresponding sulfoxide. The efficiency of reaction has been shown to be influenced by different reaction parameters such as the nature of counterion (X) and solvent as well as the molar ratio of reactants. Using Mn(TPP)OCN and ImH in 1:15 molar ratio and acetone as the solvent leads to the efficient oxidation of different sulfides.

Catalyst-free approach for solvent-dependent selective oxidation of organic sulfides with oxone

Selective oxidation of sulfides was successfully performed by employing oxone (2KHSO5·KHSO4·K2SO4) as oxidant without utilization of any catalyst/additive under mild reaction conditions. Notably, the reaction can be controlled by the chosen solvent. When ethanol was used as the solvent, sulfoxides were obtained in excellent yield; the reaction almost exclusively gave the sulfone in water. Furthermore, this protocol worked well for various sulfides to the corresponding sulfoxides in ethanol or sulfones in water.

Kinetics and mechanism of the oxidation of organic sulfides with bis(pyridine)silver permanganate

Kinetics and mechanism of the oxidation of organic sulfides with bis(pyridine)silver permanganate

Selective oxidation of organic sulfides by mononuclear and dinuclear peroxotungsten(VI) complexes

Clean conversion of a variety of sulfides and dibenzothiophene (DBT) to the corresponding sulfoxide or sulfone could be achieved in high yields at room temperature using mononuclear as well as dinuclear diperoxo complexes of tungsten as oxidants, by a variation of reaction conditions. The compounds could also effectively catalyze oxidation of sulfides by H2O2 to selectively yield sulfone with reasonably good turnover frequency (TOF).

Oxidation of organic sulfides by tetraethylammonium chlorochromate: a kinetic and mechanistic study

AbstractKeywords: correlation analysishalochromatesmechanismoxidation kineticssulfides Acknowledgements Thanks are due to the University Grants Commission, New Delhi, India, for financial support in the form of a Major Research project and to Professor Kalyan Banerji, Dean, Sciences, NLU, Mandore, Jodhpur (India).