1013-23-6

Basic information

• Product Name: Dibenzothiophene-5-oxide
• Synonyms: Dibenzothiophene-5-oxide;javascript:showMsgDetail('ProductSynonyMs.aspxCBN;dibenzo[b,d]thiophene 5-oxide
• CAS NO: 1013-23-6
• Molecular Formula: C₁₂H₈OS
• Molecular Weight: 200.25632
• Product Categories: Thiophen
• Mol File: 1013-23-6.mol
• Article Data: 177

Chemical Properties

• Melting Point: 188-188.5 °C
• Boiling Point: 400.8°Cat760mmHg
• Flash Point: 196.2°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 2.87E-06mmHg at 25°C
• Refractive Index: 1.761
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: Dibenzothiophene-5-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzothiophene-5-oxide(1013-23-6)
• EPA Substance Registry System: Dibenzothiophene-5-oxide(1013-23-6)

Safety Data

• Hazardous Substances Data: 1013-23-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of dibenzothiophenes that is the 5-oxo derivative of dibenzothiophene.

Synthesis Reference(s)

Tetrahedron, 28, p. 5017, 1972 DOI: 10.1016/0040-4020(72)88153-5

InChI:InChI=1/C12H8OS/c13-14-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14/h1-8H

Upstream product

• 132-65-0 dibenzothiophene 
• 509-14-8 tetranitromethane 
• 13029-09-9 2,2'-dibromobiphenyl 
• 597-50-2 triethylphosphine oxide 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 200875-47-4 2,8-dichlorodibenzothiophene 5-oxide 
• 62986-54-3 2-bromodibenzo[b,d]thiophene 5-oxide 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 74-88-4 methyl iodide 
• 1016-05-3 dibenzothiophene sulfone 

Downstream Products

• 65372-02-3 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline 
• 108847-24-1 dibenzo[b,d]thiophen-3-ylboronic acid 
• 97511-04-1 2-bromodibenzo[b,d]thiophene 

Relevant articles and documents

Selective oxidation of sulfides to sulfoxides using novel nano Br?nsted dicationic ionic liquid as effective reagent under grinding conditions

In this work, 1,1′-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octane-1,4-diium) bis(hydrogen sulfate) dinitrate ([C4(DABCO-H)2]·[HSO4]2[NO3]2) as a novel Br?nsted dicationic ionic liquid w

Selective Oxidation of Sulfides Catalyzed by the Nanocluster Polyoxomolybdate (NH4)12[Mo36(NO)4O108(H2O)16]

The (NH4)12[Mo36(NO)4O108(H2O)16]·30.84H2O ({Mo36}) catalyst has been synthesized and successfully employed in the selective oxidation of various sulfides to sulfoxides with urea hydrogen peroxide as oxidant under mild reaction conditions with 84-99 % conversion and 58-99 % selectivity, with active functional groups such as the hydroxy group and C=C bonds tolerated in the oxidation. The {Mo36} catalyst showed high catalytic activity for a high substrate/catalyst ratio (up to 30000:1) and is recyclable.

Self-Assembled Polyoxometalate-Based Metal-Organic Polyhedra as an Effective Heterogeneous Catalyst for Oxidation of Sulfide

Two polyoxovanadate-based metal-organic polyhedra with octahedral (oct) and rhombic dodecahedral (rdo) geometries have been constructed from a concave molecular building block and linear and triangular carboxylate ligands. VMOP-7 is constructed from {V5O9Cl} SBU and a linear anthracene-9,10-dicarboxylic acid ligand in which all the anthracene groups are perpendicular to the edge of the octahedron. Such an arrangement mode can effectively reduce the steric hindrance between ligands. VMOP-8 is constructed from {V5O9Cl} SBU and a triangular biphenyl 3,4,5-tricarboxylate ligand, which exhibits an elongated rhombic dodecahedral configuration due to the geometry of the ligand. Furthermore, VMOP-8 can serve as a heterogeneous catalyst and exhibits efficient and common catalytic activity for oxidative desulfurization.

Highly reactive magnetite covered with islands of carbon: Oxidation of N and S-containing compounds in a biphasic system

In this work a series of magnetite were prepared by impregnating of natural goethite (limonite) with glycerol before thermal treatment under N2 flow at 300, 400 and 500 °C. The formation of carbon spots (island) over magnetite was found. The magnetite was found to be the main phase after treatment at 400 and 500 °C with high content of Fe2+, which is the active specie in a Fenton like system. Furthermore, iron oxide particles with magnetic and amphiphilic properties were formed, which are interesting for using as a catalyst in refineries. All materials presented high catalytic activities for oxidation of quinoline and dibenzothiophene in a biphasic reaction system (water/toluene).

Deep oxidative desulfurization of model fuel via dielectric barrier discharge plasma oxidation using MnO2 catalysts and combination of ionic liquid extraction

This paper developed a novel oxidative desulfurization (ODS) technique via dielectric barrier discharge plasma oxidation using MnO2 catalysts and a combination of ionic liquid [BMIM]CH3COO extraction. MnO 2 catalysts were synthesized using hydrothermal synthesis and characterized using various analytical techniques. Their ODS performances were investigated. The results indicated that MnO2 catalysts could effectively improve the performance of the desulfurization system. Under optimized technical conditions, the sulfur removal of thiophene (TS), benzothiophene (BT), dibenzothiophene (DBT), and 4,6-dimethyldibenzothiophene (4,6-DMDBT) in n-octane reached 99.9%, 99.9%, 97.9%, and 90.7%, respectively. The oxidation activities of the four sulfur compounds decreased in the order of TS > BT > DBT > 4,6-DMDBT.

Accelerated Oxidation of Organic Sulfides by Microdroplet Chemistry

We report the rapid oxidation of organic sulfides to sulfoxides by means of microdroplet chemistry at room temperature using a spray solution containing an organic sulfide dissolved in water/methanol, dilute (11%-14%) sodium hypochlorite (NaClO), and 5% chloroauric acid (HAuCl4). Ultrasonic nebulization, easy ambient sonic-spray ionization, or electrosonic spray ionization serves as the microdroplet source. High-resolution mass spectrometry was used as an online detector, and nuclear magnetic resonance was used as an offline detector. We found that the sulfoxide yields vary between 66 and 95%, the highest rate of product formation is 195 mg/min for benzyl phenyl sulfoxide, and the time required is a few minutes, which is much less than that required for the conventional means of achieving this chemical transformation. We also applied this microdroplet method to protein fingerprinting. We found that protein sequences containing methionine can be quickly oxidized, providing useful information for protein structure determinations.

Single-Molecule Magnetic, Catalytic and Photoluminescence Properties of Heterometallic 3d–4f [Ln{PZn2W10O38(H2O)2}2]11? Tungstophosphate Nanoclusters

A series of eleven lanthanide containing di-Zinc (II) substituted heterometallic 3d–4f sandwich-type tungstophosphate nanoclusters [Ln{PZn2W10O38(H2O)2}2]11? (Ln=NdIII, SmIII, EuIII, GdIII, TbIII, DyIII, HoIII, ErIII, TmIII, YbIII, and LuIII) have been synthesized by a single step reaction procedure. These clusters were characterized by various analytical techniques such as single crystal X-ray diffraction (SC-XRD), fourier transform infrared (FT-IR) spectroscopy, high-resolution electro-spray ionization mass spectrometry (HR-ESI-MS), inductively coupled plasma atomic emission spectroscopy (ICP-AES), solid UV/Vis, photoluminescence spectroscopy, powder X-ray diffraction (P-XRD) and thermogravimetric analysis (TGA). All the polyanions are isostructural and consists of a lanthanide ion sandwiched between two units of (1,5) isomer of di-Zn substituted α-Keggin type tungstophosphate. The complexes Sm-2 a, Eu-3 a, Tb-5 a, and Dy-6 a show good photoluminescence behavior. The catalytic properties were examined for the oxidation of thioethers. The catalyst is stable with a high turn over frequency (TOF) of 6250 h?1 and can be recovered even after 5 consecutive cycles. Furthermore, magnetic properties revealed that Gd-4 a, Tb-5 a, Dy-6 a, Er-8 a, and Yb-10 a show single-molecule magnetic properties.

The Relative Reactivity of Thioethers and Sulfoxides toward Oxygen Transfer Reagents: The Oxidation of Thianthrene 5-Oxide and Related Compounds by MoO5HMPT

The oxidation of thianthrene 5-oxide (SSO) by MoO5HMPT has been studied in 1,2-dichloroethane at 40 deg C.Under conditions of excess substrate over the oxidant, three products are formed, i.e., two isomeric cis and trans bissulfoxides (SOSO) and sulfide-sulfone (SSO2) which quantitatively account for the active oxygen of MoO5HMPT consumed.The rates of appearance of the products at different reactant concentrations have been measured.A second-order rate law has been established.The ratios of the rate constants and of the final concentrations of the three products, i.e., k2(cis-SOSO):k2(trans-SOSO):k2(SSO2) = 1.0:4.0:1.0; infinite:infinite:infinite = 1.0:4.5:1.2, are in good agreement.The trans-SOSO-forming reaction is only 4-fold faster than that leading to SSO2. cis-SOSO and SSO2 are produced at almost the same rate.Evidence is presented that all the oxidation reactions are electrophilic processes taking place via a simple bimolecular mechanism not involving the coordination of the substrate to the metal.The low selectivity is due to the scarce reactivity of the thioether center in thianthrene 5-oxide.The investigation of the oxidative behavior of structurally related compounds reveals that such a low reactivity results from a combination of stereoelectronic effects.These findings provide a rationale to some ambiguous results obtained when thianthrene 5-oxide is employed as a mechanistic probe of the electronic character of the oxidants.

Integrated desulfurization of diesel by combination of metal-free oxidation and product removal by molecularly imprinted polymers

The production of ultra-low-sulfur diesel is an important worldwide demand. In this work a novel integrated method for desulfurization of diesel is proposed based on the combination of Bronsted acid catalyzed oxidation and the selective removal of the oxidized products using a molecularly imprinted polymer (MIP) produced in supercritical carbon dioxide (scCO2). The biphasic oxidation reaction of dibenzothiophene sulfone (DBT), as model substrate, and H2O2 as oxidant, was optimized by testing different acid catalysts, and also different phase transfer catalysts (PTC), including two different ionic liquids (ILs) trihexyl(tetradecyl)phosphoniumchloride [P6,6,6,14]Cl and Aliquat. The products of the efficient oxidation of DBT, dibenzothiophene sulfoxide (DBTSO) and dibenzothiophene sulfone (DBTSO2), were then selectively removed from real diesel using the MIP.

Nickel(II) Schiff base complex supported on nano-titanium dioxide: A novel straightforward route for preparation of supported Schiff base complexes applying 2,4-toluenediisocyanate

For the first time, a novel, straightforward and inexpensive route for immobilization of metals in Schiff base complex form is reported applying 2,4-toluenediisocyanate as a precursor of primary amine group. A nickel(II) Schiff base complex supported on nano-TiO2 was designed and synthesized as an effective heterogeneous nanocatalyst for organic reactions, and well characterized using various techniques such as Fourier transform infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy, X-ray diffraction, energy-dispersive X-ray analysis and thermogravimetric analysis. The catalytic efficiency of the complex was evaluated in selective oxidation of sulfide to sulfoxide by hydrogen peroxide as an oxidant under solvent-free conditions at room temperature, which successfully resulted in high yield and high conversion of products. Effective factors including solvent type, oxidant and catalyst amount were also optimized. The catalyst shows outstanding reusability and could be impressively recovered for six consecutive cycles without significant change of its catalytic efficiency.

Experimental and theoretical insights into the oxodiperoxomolybdenum- catalysed sulphide oxidation using hydrogen peroxide in ionic liquids

The oxidation of organic sulphides with aqueous hydrogen peroxide in ionic liquids (ILs) catalysed by oxodiperoxomolybdenum complexes was investigated. The selective formation of several sulfones was achieved using the 1:3 ratio of sulphide:H2O2 in [C4mim][PF6] (C4mim = 1-butyl-3-methylimidazolium) in a reaction catalysed by the [Mo(O)(O2)2(H2O)n] complex. Conversely, sulfoxides were produced with good selectivities using a 1:1 ratio in the same solvent in a 1 h reaction with [Mo(O)(O2) 2(Mepz)2] (Mepz = methylpyrazol). The use of [C 4mim][PF6] as the solvent was advantageous for two reasons: (i) the improved performance of the H2O2-IL combination; (ii) recycling of the catalyst/IL mixture without a significant diminution of conversion or selectivity. A DFT analysis using the [Mo(O)(O 2)2(L)] catalysts (L = Mepz, a; 3,5-dimethylpyrazole, dmpz, b; and H2O, c) indicated that a Sharpless-type outer-sphere mechanism is more probable than a Thiel-type one. The highest barrier of the catalytic profile was the oxo-transfer step, in which the nucleophilic attack of sulphide onto the peroxide ligand occurred with formation of dioxoperoxo species. In order to yield the sulfoxide and the starting catalyst, the oxidation of the resulting dioxoperoxo species with H2O2 was found to be the most favourable pathway. Subsequently, the sulfoxide to sulfone oxidation was performed through a similar mechanism involving the [Mo(O)(O2)2(L)] catalyst. The comparable energies found for the successive two oxo-transfer steps were in agreement with the experimental formation of sulfone in both the reaction with an excess of the oxidant and the stoichiometric reaction in the absence of the oxidant. In the latter case, diphenylsulfone was isolated as the major product in the 1:1 combination of diphenylsulphide and [Mo(O)(O2)2(Mepz) 2] in the ionic liquid [C4mim][PF6]. Also, the compounds [HMepz]4[Mo8O26(Mepz) 2]·2H2O, 1, [Hdmpz]4[Mo 8O26(dmpz)2]·2dmpz, 2, and [Hpz] 4[Mo8O22(O2)4(pz) 2]·3H2O, 3, were obtained by treating in water, stoichiometrically, dimethylsulfoxide and the corresponding [Mo(O)(O 2)2(L)2] complex (L = Mepz; 3,5-dimethylpyrazole, dmpz; pyrazol, pz). The crystal structures of octanuclear compounds 1-3 were indirect proof of the formation of the theoretically proposed intermediates. the Partner Organisations 2014.

Nano-sized glass as an economically viable and eco-benign support to anchor heteropolyacids for green and sustainable chemoselective oxidation of sulfides to sulfoxides

Abstract: In this work, glass wastes were employed as cost-effective supports for the immobilization of phosphomolybdic acid (5–25 wt.% PMA) through an impregnation method. The highly efficient and retrievable nanocatalyst named nano-glass waste-supported phosphomolybdic acid (n-GW/PMA) was fully characterized by several techniques such as: XRD, FE-SEM, EDX, FT-IR and TGA. The catalytic performance of the as-synthesized heterogeneous nanocatalyst was effectively investigated for the chemoselective oxidation of sulfides to sulfoxides in the presence of 30% H 2O 2 as an oxidant at room temperature under solvent-free condition. Optimization of the reaction conditions was performed by means of central composite design (CCD), which is one of the powerful response surface methodologies. Based on the results obtained under the optimum condition, the sample of 16 wt.% of PMA loading offered high conversion rates and yields (97%). Besides, the beneficial points of the prepared catalyst were its recoverability and reusability for several reaction cycles, low-cost and toxicity, easy availability and facile production. Graphical abstract: Nano-glass waste-supported phosphomolybdic acid (n-GW/PMA) was synthesized as a novel, highly efficient and retrievable nanocatalyst for the chemoselective, green and rapid oxidation of sulfides to sulfoxides through an experimental design (CCD) approach. The prepared catalyst was characterized by FT-IR, TGA, XRD, FE-SEM and EDX techniques. [Figure not available: see fulltext.].

Selective and mild oxidation of sulfides to sulfoxides or sulfones using H2O2 and Cp′Mo(CO)3Cl as catalysts

Dialkyl, aryl-alkyl, benzylic, and benzothiophenic sulfides are selectively oxidized to sulfoxides or sulfones, with stoichiometric amounts of H2O2 (aq) or TBHP, in the presence of complexes Cp′Mo(CO)3Cl, CpMoO2Cl and the mesoporous material MCM-41-2 as catalysts. The use of the thianthrene 5-oxide (SSO) probe shows that CpMo(CO)3Cl/H2O2 or TBHP are electrophilic oxidants (Xso ≤ 15). The same conclusion is drawn from competition experiments with a mixture of p-ClC6H4SCH3 and C6H5SOCH3.

Magnetic nanoparticle-supported imidazole tribromide: a green, mild, recyclable and metal-free catalyst for the oxidation of sulfides to sulfoxides in the presence of aqueous hydrogen peroxide

Imidazole tribromide immobilized on magnetic nanoparticles as a bromine source was prepared and characterized by X-ray diffraction (XRD), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), energy dispersive X-ray spectroscopy (EDX), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM) techniques. The high catalytic activity of this novel catalyst was investigated in the oxidation of sulfides to sulfoxides using aqueous hydrogen peroxide as an oxidant at room temperature under solvent-free conditions. More importantly, the catalyst could be easily recovered by an external magnet and reused five times without any significant loss of catalytic activity.

Epoxidation of alkenes and oxidation of sulfides catalyzed by a new binuclear vanadium bis-oxazoline complex

Bis(oxazoline) ligand, [2,2′-(1,3-phenylene)bis(oxazole-4,2-diyl)]-dimethanol, derived from dicyanobenzene was applied as ligand for complexation with vanadium.The catalyst was characterized by FT-IR, UV-Vis, 1H NMR spectroscopic methods, CHNS, ICP and thermal analyses, and magnetic susceptibility. The catalytic activity of this complex was then studied in the epoxidation of alkenes with TBHP (tert-butyl hydroperoxide), in acetonitrile. The effect of reaction parameters such as kind of solvent and oxygen donors was studied in the epoxidation of cyclooctene. The catalytic activity of this catalyst was also investigated in the oxidation of sulfides with H2O2 in ethanol and the corresponding sulfoxides and sulfones were produced.

Sulfuryl chloride in the synthesis of derivatives of dibenzothiophene, phenoxathiin, and thianthrene

Reactions of sulfuryl chloride with dibenzothiophene and related heterocyclic systems have been studied. It is shown that under different conditions, C- or S-halogenation of the heterocycle takes place. A series of new chlorine derivatives of dibenzothiophene, phenoxathiin and thianthrene have been synthesized and characterized. 1997 Plenum Publishing Corporation.

Selective oxidation of sulfurs and oxidation desulfurization of model oil by 12-tungstophosphoric acid on cobalt-ferrite nanoparticles as magnetically recoverable catalyst

Silica-coated CoFe2O4 nanoparticles were prepared and used as a support for the immobilization of 12-tungstophosphoric acid, to produce a new magnetically separable catalyst. This catalyst was characterized using X-ray diffraction, wavelength-dispersive X-ray spectroscopy, Fourier-transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, laser particle size analysis, and vibrating sample magnetometry. The catalyst showed high activity in the selective oxidation of thioethers and thiophenes to the corresponding sulfones under mild conditions. The catalytic activity of the nanocatalyst in the oxidative desulfurization of model oil was investigated. The effect of nitrogen-containing compounds on sulfur removal from the model oil was also evaluated. The catalyst showed high activity in the oxidative desulfurization of diesel. The catalyst can be readily isolated from the oxidation system using an external magnet and no obvious loss of activity was observed when the catalyst was reused in four consecutive runs.

N-methylpyrolidin-2-one hydrotribromide (MPHT) as a new and efficient reagent for the oxidation of sulfides to sulfoxides and sulfones

The stable and crystalline N-methylpyrolidin-2-one hydrotribromide (MPHT) effects oxidation of various sulfides to sulfoxides and sulfones. Copyright Taylor & Francis Group, LLC.

Nickel(ii) riboflavin complex as an efficient nanobiocatalyst for heterogeneous and sustainable oxidation of benzylic alcohols and sulfides

In this paper, a novel nickel-riboflavin nanocomplex has been prepared via the incorporation of Ni(OAc)2 with riboflavin. This new heterogeneous nanocatalyst showed high catalytic activity towards green oxidation reactions. The structural and m

The Pummerer-like reaction of 2,5-bis(trimethylsilyl) thiophene S-oxide with trifluoroacetic anhydride: Intermediary formation of sulfurane [10-S-4(C202)] (λ4-sulfane)

On treatment of a 2,5-bissilylsubstituted thiophene S-oxide or dibenzothiophene S-oxide with trifluoroacetic anhydride, the equilibria between the corresponding substrates and hypervalent sulfur compounds (sulfurane or λ4-sulfane) have now been first detected by low temperature NMR experiments. By elevating the temperature to room temperature, in the case of the thiophene S-oxide, the sulfurane detected was converted to 3-thiolene-2-one quantitatively via a Pummerer-like reaction.

A μ-AsO4-Bridging Hexadecanuclear Ni-Substituted Polyoxotungstate

A novel tetrahedral μ-AsO4-bridging hexadecanuclear Ni-substituted silicotungstate (ST) Na21H10[(AsO4){Ni8(OH)6(H2O)2(CO3)2(A-α-SiW9O34)2}2]·60H2O (1) was made by the reactions of trivacant [A-α-SiW9O34]10- ({SiW9}) units with Ni2+ cations and Na3AsO4·12H2O and characterized by IR spectrometry, elemental analysis, thermogravimetric analysis (TGA), and powder X-ray diffraction (PXRD). 1 contains a novel polyoxoanion [(AsO4){Ni8(OH)6(H2O)2(CO3)2(A-α-SiW9O34)2}2]31- built by four trivacant Keggin [A-α-SiW9O34]10- fragments linked through an unprecedented [(AsO4){Ni8(OH)6(H2O)2(CO3)2}2]9+ cluster, where the tetrahedral AsO4 acts as an exclusively μ2-bridging unit to link multiple Ni centers; such a connection mode appears for the first time in polyoxometalate chemistry. Furthermore, the electrochemical and catalytic oxidation properties of compound 1 have been investigated.

Deep eutectic solvent-assisted synthesis of highly efficient nanocatalyst (n-TiO2@TDI@DES (ZnCl2:urea)) for chemoselective oxidation of sulfides to sulfoxides

This study proposed a straightforward process to synthesize 2,4-toluene diisocyanate (TDI)-functionalized TiO2 nanoparticles in which a cost-effective linker (TDI) with high reactivity was employed to couple nano-TiO2 through covalent bonding to a deep eutectic solvent (DES). By this method, DES was successfully immobilized on the TiO2@TDI surface as an adsorbent and stabilizer. The structural, morphological, and physicochemical characteristics of the synthesized nanocatalysts were evaluated using various analytical methods including Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy equipped with energy-dispersive X-ray spectroscopy (SEM–EDX), and elemental analysis. The heterogeneity of the catalyst was also examined by a hot filtration test. The obtained TiO2@TDI@DES nanoparticles offered superior catalytic behavior and excellent yield as well as recyclability for the chemoselective oxidation of sulfide into sulfoxide using a green oxidant (hydrogen peroxide). This catalyst exhibited excellent reusability as it can be recovered for six successive cycles with no significant leach or reduction of catalytic efficiency.

Acidic three-liquid-phase microemulsion systems based on balanced catalytic surfactant for epoxidation and sulfide oxidation under mild conditions

Didecyldimethylammonium tungstate has been designed as a balanced catalytic surfactant to form acidic three-liquid-phase microemulsion systems at room temperature in the presence of water, a non-chlorinated solvent and dimethyldioctylammonium salts (hydrogen sulfate and dihydrogen phosphate). The triphasic system is efficient for the oxidation of olefins, sulfides and thiophenes under mild conditions. Moreover, the recovery and reusability of the catalyst, the straightforward separation of products and catalysts in two distinct phases as well as the possible use of environmentally friendly solvents such as tert-butyl acetate, make this system particularly attractive for catalytic oxidation reactions involving hydrogen peroxide as the primary oxidant under acidic or neutral conditions.

Selective and efficient oxidation of sulfides to sulfoxides using ammonium cerium (IV) nitrate in the presence of a catalytic amount of KBr or NaBr

A wide range of aliphatic or aromatic sulfides are selectively oxidized to the corresponding sulfoxides using ammonium cerium (IV) nitrate (CAN) and a catalytic amount of KBr or NaBr in the presence of wet SiO2 in CH2Cl2 u

Deep oxidative desulfurization of model oil catalyzed by magnetic MoO3/Fe3O4

A magnetic MoO3/Fe3O4 catalyst was prepared and used in the oxidative desulfurization (ODS) of dibenzothiophene (DBT), benzothiophene, and thiophene. The morphology and components of the magnetic composite material were characterized by X-ray diffraction, scanning electron microscopy and X-ray photoelectron spectroscopy techniques. Results indicated that MoO3 as an active species was supported on Fe3O4. High calcination temperature leads to the formation of Fe2(MoO4)3 compounds which showed lower activity than MoO3. The highest conversion of 99.5% for ODS of DBT can be achieved on MoO3/Fe3O4 calcinated at 400 °C. In addition, the amount of MoO3/Fe3O4, TBHP/DBT molar ratio and reaction temperature played vital roles in desulfurization efficiency. This work showed the possibility for the utilization of low cost magnetic MoO3/Fe3O4 composite in the oxidative desulfurization because it shows high activity and could be easily separated by applying an external magnetic field, achieving ten times recycling without significant decrease in activity.

Visible-light-promoted aerobic oxidation of sulfides and sulfoxides in ketone solvents

Simple and readily available ketones have been identified to promote the visible-light-promoted aerobic oxidation of sulfides and sulfoxides to sulfones. We report a simple and environmental-friendly oxidation protocol of sulfides to sulfones. Various sulfides were efficiently oxidized into sulfones with O2 as sustainable terminate oxidant, readily available thioxanthone as the photocatalyst and 3-pentanone (DEK) as the solvent. The protocol tolerates diverse functional groups, including halogens, ketone, ester, cyano, heterocycle and even cyclopropyl groups. The detection of the aerobic oxidation reaction in DEK by GC and HRMS disclosed that the key active intermediates were generated.

Niobium(V) oxido tris-carbamate as easily available and robust catalytic precursor for the selective sulfide to sulfone oxidation

The oxidation of the sulfide function promoted by a variety of vanadium compounds has been largely explored, whereas the use of homogeneous catalytic systems based on the heavier group 5 metals remains less explored. We report the use of easily available niobium and tantalum carbamates, i.e. [M(O2CNMe2)5] (M = Nb, 1; M = Ta, 2), [Nb(O2CNMe2)4], 3, [NbO(O2CNEt2)3], 4, and [NbCl3(O2CNEt2)2], 5, as effective catalysts for the conversion of a series of alkyl aryl and aromatic sulfides into the corresponding sulfones. NMR investigations on the performant niobium catalyst 4 unexpectedly revealed the substantial stability of this compound in the protic catalytic environment, and a plausible catalytic cycle was obtained by DFT studies. The two active catalytic species, i.e. 4 and its minor mono-methoxide derivative, presumably interconvert to each other exploiting the versatile coordination of the carbamato ligand.