- Organocatalytic sulfoxidation
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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.
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- Emodinas a novel organic photocatalyst for selective oxidation of sulfides under mild conditions
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Herein, we have developed naturally-occurringEmodin, which is commercially available at low-cost, as a novel organic photocatalyst for the first time.Emodinwas successfully employed in the selective oxidation of sulfides promoted by visible-light, deliver
- Li, Min,Lou, Jiangli,Rao, Yijian,Yuan, Zhenbo,Zhang, Yan
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p. 19747 - 19750
(2020/06/04)
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- Synthesis of: N -alkylated 2-pyridones through Pummerer type reactions of activated sulfoxides and 2-fluoropyridine derivatives
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N-Alkylated 2-pyridone products were obtained in good to excellent yields through a one-pot procedure involving either normal or interrupted Pummerer reactions between triflic anhydride activated sulfoxides and 2-fluoropyridine derivatives, followed by hydrolysis. This is a rare case that uses 2-fluoropyridine as a nucleophile in Pummerer type reactions.
- Hu, Gang,Xu, Jiaxi,Li, Pingfan
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p. 4151 - 4158
(2018/06/12)
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- Visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO
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The visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO is illustrated. This is the first example of DMSO being used as the source of the methylsulfinyl group. The procedure tolerates a wide range of functional groups on (het)aryl diazonium salts and provides aryl methyl sulfoxides in excellent yields under mild reaction conditions.
- Pramanik, Mukund M. D.,Rastogi, Namrata
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supporting information
p. 8557 - 8560
(2016/07/13)
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- Oxidation of organic sulfides by imidazolium fluorochromate: A kinetic and mechanistic approach
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The oxidation of organic sulfides by imidazolium fluorochromate resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to imidazolium fluorochromate. A Michaelis-Menten type kinetics was observed with respect t
- Mathur, Lokesh,Choudhary,Prakash, Om,Sharma, Pradeep K.
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p. 2597 - 2603
(2014/06/09)
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- Synergistic combination of multi-ZrIV cations and lacunary keggin germanotungstates leading to a gigantic Zr24-cluster- Substituted Polyoxometalate
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Synergistic directing roles of six lacunary fragments resulted in an unprecedented Zr24-cluster substituted poly(polyoxotungstate) Na 10K22[Zr24O22(OH) 10(H2O)2(W2O10H) 2(GeW9O34)4(GeW8O 31)2]·85H2O (Na10K 22·1·85H2O), which contains the largest [Zr24O22(OH)10(H2O)2] (Zr24) cluster in all the Zr-based poly(polyoxometalate)s to date. The most remarkable feature is that the centrosymmetric Zr24-cluster- based hexamer contains two symmetry-related [Zr12O 11(OH)5(H2O)(W2O10H) (GeW9O34)2(GeW8O31)] 16- trimers via six μ3-oxo bridges and was simultaneously trapped by three types of different segments of B-α-GeW9O34, B-α-GeW8O 31, and W2O10. The other interesting characteristic is that there are two pairs of intriguing triangular atom alignments: one is composed of the Zr(2,4,6,8,11) and W21 atoms and the other contains the Ge(1-3), Zr(3,5,7,9,10,12) and W26 atoms, and the Zr5 atom is inside the triangle; a linking mode is unobserved. The oxygenation reactions of thioethers by H2O2 were evaluated when Na 10K22·1·85H2O served as a catalyst. Results show that it is an effective catalyst for oxygenation of thioethers by H2O2. The unique redox property of oxygen-enriched polyoxotungstate fragments and Lewis acidity of the Zr cluster imbedded in Na10K22·1·85H2O provide a sufficient driving force for the catalytic conversion from thioethers to sulfoxides/sulfones.
- Huang, Ling,Wang, Sa-Sa,Zhao, Jun-Wei,Cheng, Lin,Yang, Guo-Yu
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supporting information
p. 7637 - 7642
(2014/06/10)
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- Malaria-infected mice are completely cured by one 6 mg/kg oral dose of a new monomeric trioxane sulfide combined with mefloquine
-
Sixteen new anilide derivatives of the natural trioxane artemisinin were prepared and evaluated for antimalarial efficacy in Plasmodium berghei infected mice. Of these 16 new anilides administered orally as one 6 mg/kg dose combined with 18 mg/kg mefloqui
- Slack, Rachel D.,Mott, Bryan T.,Woodard, Lauren E.,Triphati, Abhai,Sullivan, David,Nenortas, Elizabeth,Girdwood, Sonya C. T.,Shapiro, Theresa A.,Posner, Gary H.
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supporting information; experimental part
p. 291 - 296
(2012/03/10)
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- MONOMERIC TRIOXANE AMIDE SULFUR COMPOUNDS
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Anilide derivatives of the natural trioxane artemisinin were prepared and evaluated for antimalarial efficacy in Plasmodium berghei-infected mice. Selected anilides derivatives administered orally as one single-digit dose combined with mefloquine hydrochl
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Page/Page column 59
(2012/11/06)
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- Asymmetric counteranion-directed iron catalysis: A highly enantioselective sulfoxidation
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A highly active and enantioselective ion-pair sulfoxidation catalyst, consisting of an achiral iron(III)-salen cation and a chiral phosphate counteranion, mediates the oxidization of various sulfides with high yields and enantioselectivities. The enantioselectivities observed, especially for electron-poor substrates, represent the best results so far in manganese and iron-salen systems. This work represents the first application of our concept of asymmetric counteranion-directed catalysis (ACDC) to iron catalysis. Copyright
- Liao, Saihu,List, Benjamin
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supporting information
p. 2363 - 2367
(2012/10/30)
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- Oxidation of organic sulfides by tetraethylammonium chlorochromate: A kinetic and mechanistic study
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The oxidation of organic sulfides by tetraethylammonium chlorochromate (TEACC) resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to both TEACC and the sulfide. The reaction is catalyzed by toluene-p-sulfon
- Sharma, Deepika,Pancharia,Vadera,Sharma, Pradeep K.
-
experimental part
p. 315 - 326
(2012/01/04)
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- Kinetics and mechanism of the oxidation of organic sulfides with bis(pyridine)silver permanganate
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The oxidation of organic sulfides by bis(pyridine)silver permanganate (BPSP) resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to both BPSP and sulfides. The reaction is catalysed by hydrogen ions. The rat
- Banerji, Jayshree,Banerji,Kotai, Laszlo,Sharma, Deepika,Sharma, Pradeep K.
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scheme or table
p. 1879 - 1886
(2012/04/04)
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- Oligomeric iodosylbenzene sulfate: A convenient hypervalent iodine reagent for oxidation of organic sulfides and alkenes
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Oligomeric iodosylbenzene sulfate, (PhIO)3·SO 3, which can be formally considered as a partially depolymerized activated iodosylbenzene, is a readily available, stable, and water-soluble hypervalent iodine reagent that is useful for the oxidation of sulfides or alkenes. Furthermore, this reagent can be conveniently generated in situ from (diacetoxyiodo)benzene and sodium bisulfate and used without isolation in oxidations in aqueous solution or under solvent-free conditions. The reaction of iodosylbenzene sulfate in situ with organic sulfides at room temperature affords sulfoxides in high yields without over-oxidation to sulfones, and this reaction is compatible with the presence in the substrate molecule of hydroxy groups, double bonds, benzylic carbon atoms, carboxylate groups, and various substituted phenyl rings. The reaction of an alkene with iodosylbenzene sulfate generated in situ results in oxidative rearrangement to form a ketone or aldehyde. Georg Thieme Verlag Stuttgart.
- Yusubov, Mehman S.,Yusubova, Rosa Y.,Funk, Tatyana V.,Chi, Ki-Whan,Zhdankin, Viktor V.
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experimental part
p. 2505 - 2508
(2009/12/08)
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- Kinetics and mechanism of the oxidation of some organic sulfides by morpholinium chlorochromate
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The oxidation of organic sulfides by morpholinium chlorochromate (MCC) resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to both MCC and the sulfide. The reaction is catalyzed by toluene-p-sulfonic acid (T
- Malani, Neha,Baghmar, Manju,Sharma, Pradeep K.
-
experimental part
p. 65 - 72
(2009/04/07)
-
- Substituted sulphoximines as Tie2 inhibitors and salts thereof, pharmaceutical compositions comprising the same, methods of preparing the same and uses of the same
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The invention relates to substituted sulphoximines according to the general formula (I): in which A, E, G, X, R1, R2, R3, R4, R5, R6, R7, R8, m, p, q, are given in the
- -
-
Page/Page column 33
(2008/06/13)
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- ALKYNYLPYRIMIDINES AS TIE2 KINASE INHIBITORS
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The invention relates to alkynylpyrimidines according to the general formula (I) in which A, R1, R2, R3, R4, R5, and R6 are as defined in the claims, to pharmaceutical compositions comprising said alkynylpyrimidines, to methods of preparing said alkynylpyrimidines, as well as to uses thereof for manufacturing a pharmaceutical composition for the treatment of diseases of dysregulated vascular growth or of diseases which are accompanied with dysregulated vascular growth, wherein the compounds effectively interfere with Tie2 and VEGFR2 signalling.
- -
-
Page/Page column 84-85
(2009/01/23)
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- An investigation by means of correlation analysis into the mechanisms of oxidation of aryl methyl sulfides and sulfoxides by dimethyldioxirane in various solvents
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Relative rate constants have been measured for the oxidation of aryl methyl sulfides and sulfoxides by dimethyldioxirane in acetone, in mixtures of acetone with aprotic co-solvents of both higher and lower relative permittivity, and in aqueous acetone mixtures. Correlation analyses of the effects of substituents in the different solvents show that, with one exception, reactions take place via a single step mechanism in which the formation of the new SO bond and the elimination of acetone occur concertedly. The exception was oxidation of the sulfides in aqueous acetone containing the highest proportion of water of those studied (20% v/v). Here, the behaviour of the reaction is consistent with a two-step mechanism in which the oxidant reversibly attacks the sulfide to form an open-chain sulfonium betaine that subsequently fragments to sulfoxide and acetone. There is no evidence for the participation of an intermediate dioxathietane as has been found in the case of sulfide oxidations by (trifluoromethyl)methyldioxirane in CH2Cl2 and similar aprotic solvents. It is not justified to generalise a mechanism involving a betaine, with or without a derived dioxathietane, to the reactions of dimethyldioxirane in acetone. This journal is The Royal Society of Chemistry.
- Hanson, Peter,Hendrickx, Ramon A.A.J.,Smith, John R. Lindsay
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p. XX745-761
(2008/09/17)
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- SULFOXIMINE-SUBSTITUTED PYRIMIDINES , THEIR PREPARATION AND USE AS DRUGS
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The invention relates to sulfoximine-substituted pyrimidines of the general Formula (I) processes for the preparation thereof and their use as kinase inhibitors for treating for example cancer or inflammation.
- -
-
Page/Page column 142
(2010/11/27)
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- Sulfoximine-substituted pyrimidines, processes for production thereof and use thereof as drugs
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The invention relates to sulfoximine-substituted pyrimidines of the general formula I processes for the preparation thereof and their use as drugs.
- -
-
Page/Page column 54-55
(2010/11/28)
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- Kinetics and mechanism of the oxidation of organic sulphides by quinolinium bromochromate
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The oxidation of thirty-four sulphides by quinolinium bromochromate (QBC) has been found to result in the formation of the corresponding sulphoxides. The reaction is first order with respect to both QBC and the sulphide. The reaction is catalysed by hydro
- Dhariwal, Varsha,Yajurvedi, Deeksha,Sharma, Pradeep K.
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p. 1158 - 1164
(2007/10/03)
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- Efficient asymmetric oxidation of sulfides and kinetic resolution of sulfoxides catalyzed by a vanadium-salan system
-
The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium-salan [N,N′-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N′-alkylene bis(salicylideneimine) ] analogue, and provides the sulfoxide with opposite configuration. The high enantioselectivity of this reaction is the direct result of the asymmetric oxidation. The efficient kinetic resolution of racemic sulfoxides catalyzed by the vanadium-salan system is also described.
- Sun, Jiangtao,Zhu, Chengjian,Dai, Zhenya,Yang, Minghua,Pan, Yi,Hu, Hongwen
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p. 8500 - 8503
(2007/10/03)
-
- Convenient one-pot procedure for converting aryl sulfides to nitroaryl sulfones
-
When treated with nitrogen dioxide and ozone in inert solvent at 0°C or below, aryl sulfides underwent smooth oxidative nitration to give nitroaryl sulfones in good yield. Using this methodology, a series of mono- and di-nitrated aryl sulfones were prepared from methyl phenyl sulfide and diphenyl sulfide and their physical data are presented.
- Nose, Masatoshi,Suzuki, Hitomi
-
p. 1065 - 1071
(2007/10/03)
-
- Linear free energy relationships near isokinetic temperature. Oxidation of organic sulfides with nicotinium dichromate
-
The nicotinium dichromate (NDC) oxidation of methyl phenyl sulfide (MeSPh) in acetonitrile, brought about by p-toluenesulfonic acid (TsOH), is first order in NDC and TsOH, and is zero order with respect to MeSPh in the concentration range investigated. Th
- Karunakaran, Chockalingam,Chidambaranathan, Vaithiyalingam
-
-
- Kinetics and mechanism of the oxidation of organic sulfides by quinolinium fluorochromate
-
The oxidation of organic sulfides by quinolinium fluorochromate (QFC), to the corresponding sulfoxides, is first order with respect to QFC. Michaelis-Menten type kinetics were observed with respect to the sulfide. The correlation analyses of the rate of t
- Bhandari, Abhinav,Sharma, Pradeep. K.,Banerji, Kalyan K.
-
p. 653 - 675
(2007/10/03)
-
- Kinetics and correlation analysis of reactivity in oxidation of organic sulfides by hexamethylenetetramine-bromine
-
The oxidation of organic sulfides by hexamethylenetetramine-bromine (HABR) to the corresponding sulfoxides is first order with respect to HABR. Michaelis-Menten-type kinetics were observed with respect to the sulfide. It is proposed that HABR itself is th
- Choudhary, Kirti,Suri, Deepa,Kothari, Seema,Banerji, Kalyan K.
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p. 283 - 292
(2007/10/03)
-
- Lack of linear free energy relationships in the p-toluenesulfonic acid mediated chromium(VI) oxidation of organic sulfides
-
The oxidation of methylphenyl sulfide by imidazolium dichromate in acetonitrile mediated by p-toluenesulfonic acid is first order in IDC and TsOH and zero order in MeSPh in the concentration range studied. The IDC oxidation of 14 para-, meta-, and ortho-s
- Karunakaran, Chockalingam,Chidambaranathan, Vaithiyalingam
-
p. 1123 - 1128
(2007/10/03)
-
- Novel catalytic asymmetric sulfoxidation in water using the hypervalent iodine reagent iodoxybenzene
-
A new catalytic asymmetric oxidation of sulfides to sulfoxides in water using the hypervalent iodine(V) reagent iodoxybenzene (PhIO2) has been developed. This methodology is distinctly different from the previously reported use of cyclodextrins or biological catalysts and provides a new route to asymmetric sulfoxidation in water.
- Tohma, Hirofumi,Takizawa, Shinobu,Morioka, Hironori,Maegawa, Tomohiro,Kita, Yasuyuki
-
p. 445 - 446
(2007/10/03)
-
- Hypervalent Iodine(V)-Induced Asymmetric Oxidation of Sulfides to Sulfoxides Mediated by Reversed Micelles: Novel Nonmetallic Catalytic System
-
Although several types of chiral hypervalent iodine reagents have been used for asymmetric induction, all of them have needed more than a stoichiometric amount of chiral reagents and have shown low enantioselectivities. The described new catalytic asymmetric oxidation using a hypervalent iodine(V) reagent, iodoxybenzene (PhIO2), in a cationic reversed micellar system provides the first example of a catalytic asymmetric oxidation of sulfides to sulfoxides in high chemical yield with moderate to good enantioselectivity without the use of any transition-metal catalysts. The solubilization and activation of PhIO2 by adding catalytic amounts of both cetyltrimethylammonium bromide (CTAB) and a chiral tartaric acid derivative were found to be indispensable for the enhancement of chemical and optical yields.
- Tohma, Hirofumi,Takizawa, Shinobu,Watanabe, Hiroaki,Fukuoka, Yuko,Maegawa, Tomohiro,Kita, Yasuyuki
-
p. 3519 - 3523
(2007/10/03)
-
- Kinetics and Mechanism of the Oxidation of Organic Sulfides by Bis(2,2′-bipyridyl)copper(II) Permanganate
-
The oxidation of 34 sulfides by bis(2,2′-bipyridyl)copper(II) permanganate (BBCP) resulted in the formation of the corresponding sulfoxide. The reaction is first order with respect to BBCP. Michaelis-Menten type kinetics were observed with respect to the
- Bohra, Anupama,Sharma, Pradeep K.,Banerji, Kalyan K.
-
p. 3562 - 3567
(2007/10/03)
-
- Kinetics and Mechanism of the Oxidation of Organic Sulfides by Pyridinium Bromochromate
-
The oxidation of thirty-four sulfides by pyridinium bromochromate (PBC) resulted in the formation of the corresponding sulfoxides.The reaction is first order with respect to both PBC and the sulfide.The oxidation was studied in 19 different solvents.An an
- Loonker, Kavita,Sharma, Pradeep K.,Banerji, Kalyan K.
-
p. 1262 - 1285
(2007/10/03)
-
- Asymmetric oxidation of sulfides with H2O2 catalyzed by (salen)Mn(III) complexes
-
Optically active (salen)Mn(III)Cl complexes are effective catalysts for the oxidation of sulfides to sulfoxides with modest enantioselectivity. An optimal reaction system consisting of unbuffered hydrogen peroxide as the stoichiometric oxidant, acetonitri
- Palucki, Michael,Hanson, Peter,Jacobsen, Eric N.
-
p. 7111 - 7114
(2007/10/02)
-
- Kinetics and Mechanism of Oxidation of Organic Sulphides by Lead Tetraacetate
-
Kinetics of oxidation of thirty-three organic sulphides, comprising monosubstituted aryl methyl sulphides and alkyl phenyl sulphides, by lead tetraacetate (LTA), to yield the corresponding sulphoxides, have been studied.The reaction is first order with re
- Banerji, Kalyan K.
-
p. 759 - 763
(2007/10/02)
-
- MECHANISM OF THE OXIDATION OF ORGANIC SULPHIDES BY PERMANGANATE ION
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The kinetics of the oxidation of number of aryl methyl, alkyl phenyl, dialkyl and diphenyl sulphides by permanganate ion to yield the sulphoxides, have been studied.The reaction is first order with respect to the sulphide and permanganate and is independe
- Banerji, Kalyan K.
-
p. 2969 - 2976
(2007/10/02)
-
- Kinetics of the Oxidation of Organic Sulphides by Pyridinium Fluorochromate
-
The kinetics of the oxidation of a number of monosubstituted aryl methyl, alkyl phenyl, dialkyl, and diphenyl sulphides by pyridinium fluorochromate (PFC) to yield the corresponding sulphoxides have been studied.The reaction is first order with respect to
- Banerji, Kalyan K.
-
p. 2065 - 2070
(2007/10/02)
-
- Mechanism of the Oxidation of Sulphides with Sodium Periodate
-
The kinetics of the oxidation of RSAr, R2S, and (CH2)nS sulphides with NaIO4 yielding sulphoxides were investigated in ethanol-water solutions, and the rate equation v = k2 was found to be valid.The observed substituent (ρ -1
- Ruff, Ferenc,Kucsman, Arpad
-
p. 683 - 688
(2007/10/02)
-
- Substituent Effects and Mechanism of Oxidation of some Aryl Methyl Sulphides with Vanadium(V)
-
Oxidation of aryl methyl sulphides by vanadium(V) in aqueous acetic acid follows overall second order kinetics, first order each in and .Electron-donating substituents in the benzene ring accelerate the rate while electron-withdrawing one
- Satyanarayana, P. V. V.,Rao, Y. Nageswara,Rao, N. Nageswara
-
-