- Electrochemical oxidation of sulfinic acids: Efficient oxidative synthesis of diaryl disulfones
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Electrochemical oxidation of sulfinic acids has been studied in aqueous solutions using cyclic voltammetry, controlled-potential coulometry, chronoamperometry and chronocoulometry methods. The results indicate that the oxidation of sulfinic acids is an ir
- Nematollahi, Davood,Joudaki, Mahsa,Khazalpour, Sadegh,Pouladi, Firozeh
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- I2-Catalyzed N-Sulfonylation of Sulfoximines with Sulfinates in Water at Room Temperature
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An oxidative coupling of NH-sulfoximines and arylsulfinates catalyzed by of I2 and H2O2 affords N-sulfonyl sulfoximines. The reaction proceeds under aerobic conditions in water at room temperature. The merits of this proto
- Zheng, Wenting,Tan, Mingchao,Yang, Lu,Zhou, Lihong,Zeng, Qingle
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- Sonochemical Preparation of Aromatic α-Disulfones
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Reasonable yields (60-70percent) of aromatic α-disulfones can be obtained in short reaction times from a sonicated mixture of an arenesulfonyl chloride and lithium in THF. - Key Words: Alpha-disulfones, sonication, Wurtz-type coupling
- Prokes, Ivan,Toma, Stefan,Luche, Jean-Louis
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- A paradigm shift in rate determining step from single electron transfer between phenylsulfinylacetic acids and iron(III) polypyridyl complexes to nucleophilic attack of water to the produced sulfoxide radical cation: a non-linear Hammett
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Mechanism of oxidative decarboxylation of phenylsulfinylacetic acids (PSAAs) by iron(III) polypyridyl complexes in aqueous acetonitrile medium has been investigated spectrophotometrically. An initial intermediate formation between PSAA and [Fe(NN)3]3+ is confirmed from the observed Michaelis–Menten kinetics and fractional order dependence on PSAA. Significant rate retardation with concentration of [Fe(NN)3]3+ is rationalized on the basis of coordination of a water molecule at the carbon atom adjacent to the ring nitrogen of the metal polypyridyl complexes by nucleophilic attack at higher concentrations. Electron-withdrawing and electron-releasing substituents in PSAA facilitate the reaction and Hammett correlation gives an upward ‘V’ shaped curve. The apparent upward curvature is rationalized based on the change in the rate determining step from electron transfer to nucleophilic attack, by changing the substituents from electron-releasing to electron-withdrawing groups. Electron-releasing substituents in PSAA accelerate the electron transfer from PSAA to the complex and also stabilize the intermediate through resonance interaction leading to negative reaction constants (ρ). Conversely, electron-withdrawing groups, while retarding the electron transfer exert an accelerating effect on the nucleophilic attack of H2O which leading to low magnitude of ρ+ compared to high ρ? values of electron-releasing groups. Marcus theory is applied, and a fair agreement is seen with the experimental values. Copyright
- Subramaniam, Perumal,Janet Sylvia Jaba Rose, Jebamoney,Jeevi Esther Rathinakumari, Rajasingh
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p. 496 - 504
(2016/09/21)
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- Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide
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A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).
- Zheng, Yong,Qing, Feng-Ling,Huang, Yangen,Xu, Xiu-Hua
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supporting information
p. 3477 - 3481
(2016/11/13)
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- Synthesis of 1,1-difluoroethylsilanes and their application for the introduction of the 1,1-difluoroethyl group
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1,1-Difluoroethysilanes (R3SiCF2CH3, R = Me or Et) were synthesized from 1,1-difluoroethyl phenyl sulfone and chlorosilanes using magnesium metal via reductive 1,1-difluoroethylation. It was confirmed that 1,1-difluoroethylsilanes were effective 1,1-difluoroethylating reagents for carbonyl compounds.
- Mogi, Ryo,Morisaki, Kazuo,Hu, Jinbo,Prakash, G.K. Surya,Olah, George A.
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p. 1098 - 1103
(2008/02/09)
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- Temperature-controlled selective reduction of arenesulfonyl chlorides promoted by samarium metal in DMF
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Promoted by samarium in DMF, arenesulfonyl chlorides can be selectively reduced to diaryldisulfones, diarylthiosulfonates and diaryldisulfides in good to excellent yields by reaction temperature control without the need to pretreat or activate the metallic samarium.
- Liu, Yongjun,Zhang, Yongmin
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p. 4291 - 4294
(2007/10/03)
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- Oxidation of thiols with hydrogen peroxide under phase transfer catalysis conditions
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Theophenol was shown to be oxidized with hydrogen peroxide under conditions of phase transfer catalysis in the presence of sodium metavanadate to afford benzenesulfonic acid, diphenyl disulfide, phenyl benzenesulfonate, and diphenyl sulfone. The yield of oxidation products increases with increasing temperature, catalyst concentration, and lipophilicity of the phase transfer catalyst.
- Lesnugin,Anisimov,Tarakanova
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p. 423 - 425
(2007/10/03)
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- OXIDATION OF 1,2-bis-(BENZENESULFONYL)HYDRAZINE TO 1,2-DIPHENYLDISULFONE
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The oxidation of 1,2-bis(benzenesulfonyl)hydrazine yields diphenyldisulfone and not 1,2-bis(benzenesulfonyl)diimide as previously reported.
- Maioli, Andrew T.,Anselme, Jean-Pierre
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p. 1221 - 1222
(2007/10/02)
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- OXIDATION OF DISULPHIDES BY HYDROGEN PEROXIDE IN THE PRESENCE OF SUBSTITUTED PHTHALOCYANINES OF TRANSITION METALS
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A study has been made of the oxidation of disulphides of different structure by hydrogen peroxide in the presence of nitrosubstituted phthalocyanines of transition metals.It has been established that phthalocyanines in a homophase system ensure a higher initial oxidation rate of disulphides to disulphones and thiosulphonates than Na2WO4 in a two-phase system with the use of interphase transfer catalysts.
- Anisimov, A. V.,Mohammed, R. A.,Borisenkova, S. A.,Tarakanova, A. V.,Barkanova, S. V.,Et Al.
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p. 347 - 352
(2007/10/02)
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- OXIDATION OF DISULPHIDES BY HYDROGEN PEROXIDE UNDER INTERPHASE CATALYSIS CONDITIONS
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It has been shown that aliphatic and aromatic disulphides are oxidized by hydrogen peroxide in the presence of sodium tungstate and molybdate and an interphase catalyst to the corresponding thiolsulphonates and disulphones.The structure of the oxidation products depends on the interphase catalyst used: in the presence of triethylbenzylammoniumbromide, thiosulphonates are formed, while in the presence of cetyltrimethylammoniumbromide, disulphones are formed.The main reason for this difference is the solubility in the organic phase of the intermediate peroxy complex formed by the reaction of hydrogen peroxide with the metal compound in the presence of phosphoric acid.The rate of the reaction and the yields of oxidation products depend on the temperature, the solvent used and the ratio of the reactants.
- Anisimov, A. V.,Mohammed, R. A.,Tarakanova, A. V.,Borisenkova, S. A.
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p. 407 - 412
(2007/10/02)
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- A facile and general method for the preparation of α-disulfones (R1SO2SO2R2)
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Dialkyl, diaryl and alkyl aryl disulfones are easily prepared by oxidation of N,N'-disulfonylhydrazines with nitric acid. The method is compatible with a wide variety of substituents (R1,R2) on the sulfur atoms.
- Bartmann
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p. 490 - 496
(2007/10/02)
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- Molecular Rearrangements. XXVI. Thermolysis and Photolysis of Arenesulphohydroxamic Acids
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Thermolysis of arenesulphohydroxamic acid (Ar=Ph or p-tolyl) by heating at its melting point in air for 10 min gave nitric oxide, sulphurdioxide, and ammonia together with the corresponding arene, biaryl, diaryl sulphide, diaryl disulphide, diaryl sulphone, diaryl disulphone, thiophenol, aryl ammonium sulphonate, arene sulphonic acid and ammonium sulphite.Similar results were obtained on photolysis in acetone solution for 20 h at room temperature.The photolysis was found to be an intramolecular process as shown by cross-over experiment.A free-radical mechanism starting by homolysis of the S-N bond was suggested to account for the observed results.
- Aly, M. M.,Fahmy, A. M.,Abdel-Latif, F. F.,Badr, M. Z. A.
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