cas 14090-83-6, METHYL (PHENYLSULFINYL)ACETATE

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A magnetic supported iron complex for selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide at room temperature
A magnetic supported iron (iron(ii) acetylacetonate) was synthesized to be used as an efficient and recyclable heterogeneous catalyst for the selective oxidation of sulfides to corresponding sulfoxides using H2O2 as a green oxidant at room temperature. The synthesized Fe3O4@SiO2-APTES(Fe(acac)2) catalyst presented excellent sulfide conversion and good sulfoxide selectivity. It can be easily recovered and reused for 8 reaction cycles without considerable loss of activity. The facile recovery of the catalyst is carried out by applying an external magnet device. The catalyst was fully characterized by techniques of TEM, SEM, XRD, EDS, FTIR, TGA, ICP-AES, VSM and elemental analysis (CHN).
Bayat, Ahmad,Shakourian-Fard, Mehdi,Ehyaei, Nona,Hashemi, Mohammad Mahmoodi
p. 44274 - 44281
(2014)
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Organocatalytic sulfoxidation
Treatment of a sulfide with a catalytic amount of a 1,3-diketone in the presence of silica sulfuric acid as a co-catalyst and hydrogen peroxide (50% aq) as the stoichiometric oxidant leads to the corresponding sulfoxide product. The reaction is effective for diaryl, aryl-alkyl and dialkyl sulfides and is tolerant of oxidisable and acid sensitive functional groups. Investigations have shown that the tris-peroxide 2, formed on reaction of pentane-2,4-dione with hydrogen peroxide under acidic reaction conditions, can oxidise two equivalents of sulfide using the exocyclic peroxide groups whereas the endocyclic peroxide remains intact. Calculations provide a mechanism consistent with experimental observations and suggest the reaction proceeds via an initial acid catalysed ring opening of a protonated tris-peroxide prior to oxygen transfer to a sulfur nucleophile.
Davidson, Stuart C.,Gomes, Gabriel dos Passos,Kuhn, Leah R.,Alabugin, Igor V.,Kennedy, Alan R.,Tomkinson, Nicholas C.O.
(2020/12/07)

Tungstate supported mesoporous silica SBA-15 with imidazolium framework as a hybrid nanocatalyst for selective oxidation of sulfides in the presence of hydrogen peroxide
In this work, a new heterogeneous catalyst (SBA-15/Im/WO4 2?) was prepared, and then its performance in the oxidation of organic sulfides was studied (using 30% H2O2 as green oxidant under neutral reaction conditions). This organic–inorganic hybrid mesoporous material was characterized by various techniques, such as FT-IR, inductively coupled plasma, X-ray powder diffraction, high-resolution-transmission electron microscopy, N2 adsorption–desorption and thermogravimetric analysis. The catalyst was also applied to the selective oxidation of various sulfides. The hybrid catalyst was easily recovered, and was very stable and retained good activity for at least five successive runs without any additional activation. Moreover, there was no remarkable decrease in the activity and selectivity of the catalyst. The products could be easily isolated by just removing the solvent after filtering the catalyst. The yields of the catalytic productions through this catalyst were in the range from 75% to 97%.
Sedrpoushan, Alireza,Hosseini-Eshbala, Fereshteh,Mohanazadeh, Farajollah,Heydari, Masoud
(2017/09/07)

Schiff base Mn(III) and Co(II) complexes coated on Co nanoparticles: An efficient and recyclable magnetic nanocatalyst for H2O2 oxidation of sulfides to sulfoxides
In this paper, an effective and selective heterogeneous catalyst was produced by immobilization of manganese and cobalt Schiff base-complexes on Co magnetite nanoparticles (MNP). The catalysts Co@SiO2[(EtO)3Si-L3]/M (M = Mn(iii) and Co(ii)) were synthesized using Co@SiO2 core-shell nanoparticles and amino-functionalized Co@SiO2. The Schiff base ligand Co@SiO2[(EtO)3Si-L3] was synthesized by reacting Co@SiO2 core-shell nanoparticles with 2-hydroxy 1-naphthaldehyde for the synthesis of Co@SiO2[(EtO)3Si-L3]/M. The catalysts were characterized by several techniques, such as FT-IR, TEM, XRD, TGA and VSM. The catalytic activities of the prepared catalysts were studied by oxidation of sulfides to the sulfoxides under different conditions. These catalysts can be easily recovered and reused in at least seven sequential cycles without considerable leaching and loss of reactivity.
Saremi, Shokoufeh Ghahri,Keypour, Hassan,Noroozi, Mohammad,Veisi, Hojat
p. 3889 - 3898
(2018/02/07)

α-Benzoyloxylation of β-keto sulfides at ambient temperature
A facile and efficient protocol for the α-benzoyloxylation of β-keto sulfides is presented. This methodology provides a step-economical, mild and practical access to highly functionalized α-O-benzoyloxy substituted β-keto sulfides, including those with quaternary carbons, which are not easily obtained through currently available methods.
Piras, Enrico,Secci, Francesco,Caboni, Pierluigi,Casula, Maria Francesca,Frongia, Angelo
p. 49215 - 49219
(2017/11/03)

Application of sodium titanate nanotubes doped with vanadium (VNaTNT) as a heterogeneous catalyst for oxidation of sulfides at room temperature
A heterogeneous titanate nanotube (TNT) catalyst containing TiO2, Na, and V has been synthesized and used in the chemoselective oxidation of sulfides to the corresponding sulfoxides in the presence of 30% H2O2 in water. Some of the advantages of our method include excellent yields, heterogeneous conditions, simplicity, compatibility with a variety of functionalities, and ease of isolation of the products. Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, and N2 adsorption were used for structural and textural characterization of the catalyst (VNaTNT).
Dadvar, Mohammad Ali,Fazaeli, Razieh
p. 494 - 501
(2016/04/20)

Synthesis and Photocatalytic Reactivity of Vinylsulfonium Ylides
Although sulfur ylides are textbook reagents in organic synthesis, surprisingly little variation of substituents on sulfur is usually observed. In particular, vinylsulfonium ylides have been neglected so far. Herein, we present a study on their synthesis and reactivity, including interesting behavior under photocatalytic conditions.
Klose, Immo,Misale, Antonio,Maulide, Nuno
p. 7201 - 7210
(2016/09/04)

Application of 1,4-bis(3-methylimidazolium-1-yl)butane ditribromide [bMImB]·(Br3)2 ionic liquid reagent for selective oxidation of sulfides to sulfoxides
1,4-Bis(3-methylimidazolium-1-yl)butane ditribromide [bMImB]·(Br3)2 as an efficient reagent is used for the selective oxidation of dialkyl and alkyl aryl sulfides to the corresponding sulfoxides in high yields under mild conditions. The products can easily be isolated by just washing the highly water soluble 1,4-bis(3-methylimidazolium-1-yl)butane ditribromide [bMImB]·(Br3)2. The spent reagent can be recovered several times and reused without any significant loss.
Manesh, Abbas Amini,Eshbala, Fereshteh Hosseini,Hemmati, Saba,Veisi, Hojat
p. 70265 - 70270
(2015/09/07)

Polyoxomolybdate-Calix[4]arene Hybrid: A Catalyst for Sulfoxidation Reactions with Hydrogen Peroxide
An easily accessible polyoxomolybdate-calix[4]arene hybrid 1 has been synthesized and applied as a heterogeneous catalyst in the sulfoxidation of thioethers to sulfoxides and to sulfones under strictly stoichiometric amounts of 30% H2O2 in CH3CN as the solvent. This study represents the first promising example of successful employment of calixarenes-polyoxometalate (POM) hybrid materials in the area of catalytic oxidations.
Meninno, Sara,Parrella, Alessandro,Brancatelli, Giovanna,Geremia, Silvano,Gaeta, Carmine,Talotta, Carmen,Neri, Placido,Lattanzi, Alessandra
supporting information
p. 5100 - 5103
(2015/11/03)

Nano-rod catalysts: Building MOF bottles (MIL-101 family as heterogeneous single-site catalysts) around vanadium oxide ships
Porous materials based on chromium (III) terephthalate metal organic frameworks (Cr-MIL(101)) and their new composites with vanadium oxide has emerged as a potential catalyst because of its high specific surface area, tunable pore size, and unique structure. The structural and textural characterization of V@MIL(101) were done using FTIR, X-ray diffraction, N 2 adsorption-desorption, and TEM. XRD and adsorption-desorption analysis shows that the mesostructure of MIL-101 remains intact after vanadium oxide modifications, while spectral technique show the successful immobilizing of the neat vanadium oxide inside the MIL-101 cavities. These new catalysts were found to be highly effective for selective oxidation of sulfides to sulfoxides and sulfones with H2O2 at room temperature and the 4.2% V@MIL(101) catalyst showed the highest activity. The PW12@MCF im heterogeneous system showed high catalytic oxidative activity in the treatment of commodity gasoline.
Fazaeli, Razieh,Aliyan, Hamid,Moghadam, Majid,Masoudinia, Mona
p. 46 - 52
(2013/06/27)

Oxidation reactions catalyzed by polyoxomolybdate salts
Ionic compounds containing the polyoxomolybdate anion [Mo6O 19]2- and [(n-C4H9) 4P]+ (tetra-butylphosphonium), [(n-C4H 9)3P(n-C14H29)]+ (tributyl (tetradecyl)phosphonium), [Bmim]+ (1-butyl-3- methylimidazolium) and [Dbmim]+ (1,2-dimethyl-3-butylimidazolium) cations were prepared and characterized, including the determination of three of the solid state structures by singlecrystal X-ray diffraction. These compounds were applied as catalysts for the epoxidation of olefins with urea hydrogen peroxide (UHP) as oxidant in the ionic liquid [Bmim]PF6. Additionally, the oxidation of sulfides to sulfoxides with hydrogen peroxide (H2O2) in several solvents was investigated. The polyoxomolybdate catalysts showed a good performance for epoxidation of olefins as well as for oxidation of sulfides. Furthermore, the catalysts can be recycled several times in oxidation reactions. We present this methodology for the oxidation reaction in a simple, economically, technically, and environmentally benign manner.
Zhang, Bo,Li, Su,Poethig, Alexander,Cokoja, Mirza,Zang, Shu-Liang,Herrmann, Wolfgang A.,Kuehn, Fritz E.
p. 587 - 597
(2013/07/26)

Cyclic seleninate esters as catalysts for the oxidation of sulfides to sulfoxides, epoxidation of alkenes, and conversion of enamines to α-hydroxyketones
Cyclic seleninate esters serve as catalysts for the rapid oxidation of sulfides to sulfoxides, alkenes to epoxides, and enamines to α-hydroxyketones. Optimal conditions were found that minimize the overoxidation of the product sulfoxides to sulfones and the hydrolysis of epoxides to diols. In some examples such as styrene derivatives, oxidative cleavage was observed instead of epoxidation. The enamine oxidations proceed via the initial formation of dimeric 2,5-diamino-1,4-dioxane species, which were hydrolyzed in situ to the final products. The structure of one such dimer was confirmed by X-ray crystallography.
Mercier, Eric A.,Smith, Chris D.,Parvez, Masood,Back, Thomas G.
experimental part
p. 3508 - 3517
(2012/06/04)

Host (aluminum incorporated mesocellulous silica foam (Al-MCF))-guest (tungsten polyoxometalate) nanocomposite material: An efficient and reusable catalyst for selective oxidation of sulfides to sulfoxides and sulfones
A green, efficient and selective approach for the oxidation of sulfides to sulfoxides and sulfones with H2O2 at room temperature is reported. The reaction is performed in the presence of tungstophosphoric acid (PW12) supported on an aluminum incorporated mesocellulous silica foam (Al-MCF) (via both: the impregnation and encapsulation methods), as heterogeneous and reusable catalysts. The structural and textural characterizations of these catalysts were done using FTIR, X-ray diffraction, N2 adsorption-desorption and TEM.
Fazaeli, Razieh,Aliyan, Hamid,Ahmadi, Mohammad Ali,Hashemian, Saeedeh
p. 48 - 52
(2013/01/15)

Oxidation of sulfides to sulfoxides with H2O2/HNO3 reagent system
Selective oxidation of sulfides to sulfoxides is achieved by H2O2 using HNO3 as the promotor. Aromatic and aliphatic sulfides are oxidized to sulfoxides in excellent yields and short reaction times. Different functional groups including C-C double bond, ester, ketone, acetal, alcohol, and oxime groups are tolerated under this reaction condition.
Khodaei, Mohammad Mehdi,Bahrami, Kiumars,Arabi, Mehdi Sheikh
experimental part
p. 83 - 88
(2010/10/20)

TMSCl-promoted selective oxidation of sulfides to sulfoxides with hydrogen peroxide
Selective oxidation of sulfides to sulfoxides is achieved using H 2O2 and TMSCl as the promotor. Aromatic and aliphatic sulfides are oxidized to sulfoxides in excellent yields and in short reaction times. Different functional groups including ketone, alkene, ester, and alcohol are tolerated.
Bahrami, Kiumars,Khodaei, Mohammad M.,Yousefi, Behrooz H.,Arabi, Mehdi Sheikh
experimental part
p. 6939 - 6941
(2011/03/17)

TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides
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
supporting information; experimental part
p. 6208 - 6213
(2010/11/04)

Efficient and highly selective oxidation of sulfides to sulfoxides in the presence of an ionic liquid containing hypervalent iodine
A mild, efficient, highly selective, and environmentally friendly oxidation of sulfides to sulfoxides with a recyclable ion-supported hypervalent iodine reagent has been developed. This reaction is tolerant of hydroxyl, nitrile, methoxy, carbon-carbon double bonds, and ester functionalities. Aliphatic and aromatic sulfides are selectively oxidized to the corresponding sulfoxides at room temperature in excellent yields. Georg Thieme Verlag Stuttgart.
Qian, Weixing,Pei, Lin
p. 709 - 712
(2007/10/03)

Selective and mild oxidation of sulfides to sulfoxides by oxodiperoxo molybdenum complexes adsorbed onto silica gel
Aliphatic and aromatic sulfides, ketosulfides, sulfinyl acids and esters, and olefinic sulfides were oxidized to sulfoxides using oxodiperoxo complexes of molybdenum coated on silica gel (150 ? pore size) in very high yields. Complete chemoselectivity was observed for the oxidation of all functional sulfides. Sulfones were, however, the main products of the reaction when the complexes were not coated on silica gel. The influence of silica gel as the support of these reactions was also investigated and it was demonstrated that it alters the reactivity of the complex but it is not responsible for the excellent chemoselectivity of the complexes. The complex [MoO(O2)2(pyrazole) (H2O)] proved to be more reactive than [MoO(O2)2(Opyr) (H2O)].
Batigalhia, Fabiana,Zaldini-Hernandes, Marcelo,Ferreira, Ant?nio G,Malvestiti, Ivani,Cass, Quezia B
p. 9669 - 9676
(2007/10/03)

Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane) peroxodisulfate: A mild and efficient oxidant for oxidation of thiols, sulfides and aromatic amines to the corresponding disulfides, sulfoxides and azo compounds
Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane) peroxodisulfate (BAABCPS) 1, readily prepared as orange solid from commercially available 1,4-diazabicyclo[2.2.2]octane (DABCO) and potassium peroxodisulfate converts thiols, sulfoxides and aromatic amines to the corresponding disulfides, sulfoxides and azo compounds respectively.
Hajipour,Mohammadpoor Baltork,Kianfar
p. 607 - 610
(2007/10/03)

1-Benzyl-1-aza-4-azoniabicyclooctane periodate as new oxidant for oxidation of thiols and sulfides to the corresponding disulfides and sulfoxides under anhydrous conditions
1-Benzyl-1-aza-4-azoniabicyclooctane periodate (BAABCOP) 1, readily prepared as an orange solid from commercially available DABCO (1,4-diazobicyclooctane) performs oxidation in anhydrous conditions. Under these conditions, thiols are selectively oxidised to disulfides. Sulfides are also oxidised to the corresponding sulfoxides under these conditions.
Hajipour, A. R.,Mahboubghah, N.
p. 1041 - 1043
(2007/10/03)

Solid state oxidation of aromatic sulfides to corresponding phenyl and p-tolyl sulfoxides and sulone using oxone
Phenyl and p-tolyl sulfides 1 can be selectively oxidised to the corresponding sulfoxides 2 or sulfones 3 in solid state condition using oxone. The advantages of this method are the use of cheap and safe reagents, high yield and simple operating conditions.
Hajipour, A. R.
p. 1069 - 1070
(2007/10/03)

Reactions on solid supports: Oxidation of sulfides to sulfoxides catalyzed by metalloporphyrins supported on silicagel
The use of metalloporphyrins immobilized on silica, with iodosylbenzene as oxidant, leads to a selective oxidation of sulfides to sulfoxides.
Pautet,Daudon
p. 1457 - 1458
(2007/10/02)

A FACILE ROUTE TO HOMOCHIRAL SULFOXIDES
Biocatalytic resolution of methyl sulfinylacetates afford sulfoxides (R)-(1)-(6) in very high optical yields; the products have been used in a systematic study of the "SPAC" reaction, an asymmetric synthesis of γ-hydroxy-α,β-unsaturated esters.
Burgess, Kevin,Henderson, Ian
p. 3633 - 3636
(2007/10/02)

OXIDATION OF SULFIDES BY IODYLARENES IN THE PRESENCE OF VANADYL ACETONYLACETONATE AS A CATALYST
Key words: Sulfide oxidation; sulfoxide; iodylarene; vanadyl acetylacetonate.Iodylbenzene is a poor oxidant of sulfur, but in the presence of vanadyl acetylacetonate, sulfides are converted into sulfoxides, sulfones and S-dealkylated products.To improve the selectivity and the yield of this reaction, different substituted iodylarenes are used.The N-(paraiodylphenyl) palmitoylamid is a promising oxidant for synthetic purposes.
Barret, R.,Pautet, F.,Bordat, P.,Tinland, B.,Daudon, M.
p. 31 - 34
(2007/10/02)

NUCLEOPHILIC REACTIONS AT A VINYL CENTER. XIV. REACTION OF β,β-DICHLOROVINYL PHENYL SULFOXIDE WITH SODIUM METHOXIDE AND THIOPHENOLATES
The kinetics of the nucleophilic substitution of chlorine atoms in β,β-dichlorovinyl phenyl sulfoxide by sodium methoxide and substituted thiophenolates in methanol were investigated.The substitution of the first chlorine atom in reaction with sodium methoxide is realized by an elimination-addition mechanism, while substitition of the second chlorine atom is realized by a direct substitution mechanism.In the reaction with sodium thiophenolates both chlorine atoms are substituted by a direct substitution mechanism.A comparison is made of the reactivities of β,β-dichlorvinyl phenyl sulfoxide and β,β-dichlorovinyl phenyl sulfone, and the effect of the activating group at the α position is discussed.
Shainyan, B. A.,Mirskova, A. N.
p. 283 - 287
(2007/10/02)

Synthesis of stable prostacyclin analogues
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Galambos,Simonidesz,Ivanics,et al.
p. 1281 - 1284
(2007/10/02)

EFFECT OF MOLECULAR STRUCTURE ON OPTICAL PROPERTIES OF SULFOXIDE SYSTEMS. PHENYL- AND m-BROMOPHENYLSULFINYLACETIC ACIDS AND SOME OF THEIR DERIVATIVES. PART I
The synthesis of phenylsulfinyl- and sulfonyl-acetic acids and their m-bromo derivatives is described.The racemic sulfoxides were resolved into enantiomers.The absolute configurations of enantiomers were elucitated.The optical rotatory dispersion of laevorotatory enantiomers, their amides, p-nitrobenzyl and p-bromophenacyl esters was determined.
Janczewski, Marian,Najda, Teresa,Jablonska-Pikus, Teresa
p. 1297 - 1312
(2007/10/02)

2. 2. 0.
Two new syntheses of cyclobutene esters and the use of 1-cyanocyclobutene as potential isoprene synthons are described. Photocycloaddition of methyl cyclobut-1-enecarboxylate and 1-cyanocyclobutene to piperitone, followed by reduction and lactonization, gives photodihydroarisolactone. Single-crystal X-ray analysis of the latter and a related compound reveals interesting structural features in the strained bicyclo left bracket 2. 2. 0 right bracket hexane system. Thermolysis of these lactones yields 1,5-cyclodecadienes related to germacrene sesquiterpenes.
Wilson,Phillips,Pelister,Huffman
p. 7373 - 7379
(2007/10/06)