- Alumina supported nanoruthenium as efficient heterogeneous catalyst for the selective H2O2 oxidation of aliphatic and aromatic sulfides to sulfoxides
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Highly stable polyvinylpyrrolidone (PVP) capped ruthenium nanoparticles (RuNPs) supported on γ-Al2O3 in CH3CN serve as efficient heterogeneous catalysts for the H2O2 oxidation of sulfides into the cor
- Veerakumar,Lu, Zong-Zhan,Velayudham,Lu, Kuang-Lieh,Rajagopal
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experimental part
p. 128 - 137
(2010/12/25)
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- Efficient aerobic oxidation of phosphines, phosphites, and sulfides by using trialkylborane
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Treatment of phosphines, phosphites, or sulfides with trialkylborane under air afforded the corresponding oxides in good yields.
- Motoshima, Kosuke,Sato, Akinori,Yorimitsu, Hideki,Oshima, Koichiro
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experimental part
p. 2229 - 2231
(2009/08/08)
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- Electron transfer reactions of tris(polypyridine)ruthenium(III) complexes with organic sulfides: Importance of hydrophobic interaction
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Ruthenium(III)-polypyridyl complexes, generated from the photochemical oxidation of Ru(II) complexes with molecular oxygen, undergo facile electron transfer reaction with dialkyl and aryl methyl sulfides. The rate controlling electron transfer process is
- Ganesan, Muniyandi,Sivasubramanian, Veluchamy K.,Rajendran, Thangamuthu,Swarnalatha, Kalaiyar,Rajagopal, Seenivasan,Ramaraj, Ramasamy
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p. 4863 - 4871
(2007/10/03)
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- Synthesis of Sulfoxides by the Hydrogen Peroxide Induced Oxidation of Sulfides Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin: Scope and Chemoselectivity
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The oxidation of sulfides with H2O2 catalyzed by iron tetrakis(pentafluorophenyl)porphyrin in EtOH is an efficient and chemoselective process. With a catalyst concentration 0.03-0.09% of that of the substrate, sulfoxides are obtained with yields generally around 90-95% of isolated product. With vinyl and allyl sulfides, no epoxidation is observed. With a catalyst concentration between 0.09% and 0.25% of that of the substrate, sulfones are obtained in almost quantitative yield and with the same high chemoselectivity observed in the synthesis of sulfoxides.
- Baciocchi, Enrico,Gerini, Maria Francesca,Lapi, Andrea
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p. 3586 - 3589
(2007/10/03)
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- Mechanism of selective oxidation of organic sulfides with oxo(salen)chromium(V) complexes
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The selective oxidation of organic sulfides to sulfoxides by oxo(salen)chromium(V) complexes in acetonitrile is overall second-order, first-order each in the oxidant and the substrate. The rate constant, k2, values of several para-substituted p
- Sevvel, Ranganathan,Rajagopal, Seenivasan,Srinivasan, Chockalingam,Alhaji, Nainamohamed Ismail,Chellamani, Arunachalam
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p. 3334 - 3340
(2007/10/03)
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- A mild, inexpensive, and convenient synthesis of sulfoxides by the oxidation of sulfides with calcium hypochlorite and moist alumina
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The dichloromethane-alumina biphasic system is a simple and effective reagent for the selective oxidation of sulfides to the sulfoxides with calcium hypochlorite.
- Hirano, Masao,Yakabe, Sigetaka,Itoh, Shikiko,Clark, James H.,Morimotoa, Takashi
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p. 1161 - 1164
(2007/10/03)
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- Synthesis of sulfoxides by the oxidation of sulfides with sodium chlorite catalysed by manganese(III) acetylacetonate in acetone in the presence of alumina
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Systematic oxidations of sulfides with sodium chlorite have been investigated in aprotic solvents under mild and neutral conditions.Metal catalysis is essential for the efficient oxidation, and conversion of a wide variety of diaryl, alkyl aryl, dialkyl and cyclic sulfides into the corresponding sulfoxides can be favoured by the catalytic presence of manganese(III) acetylacetonate in acetone with the aid of moist alumina in general or dry alumina in particular cases in a rapid, high-yielding manner.This simple procedure has also been found to be an easy method for chemoselective transformation of functionalised sulfides without extensive undesirable side-reactions.
- Hirano, Masao,Yakabe, Shigetaka,Clark, James H.,Morimoto, Takashi
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p. 2693 - 2698
(2007/10/03)
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- N-Hydroxy-o-benzenedisulfonimide: A misunderstood selective oxidizing agent
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N-Hydroxy-o-benzenedisulfonimide (now an easily accessible reagent) is a useful selective oxidizing agent; this is contrary to what was previously believed. The oxidation reactions of aldehydes to acids, benzyl alcohols to aldehydes, thiols to disulfides, and sulfides to sulfoxides were investigated (18 examples).
- Barbero, Margherita,Degani, Lacopo,Fochi, Rita,Perracino, Paolo
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p. 8762 - 8764
(2007/10/03)
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- Oxidation with mercury(II) oxide-iodine reagent: Selective oxidation of sulfides to sulfoxides
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A new method for selective oxidation of sulfides to sulfoxides with mercury(II) oxide-iodine reagent is reported.
- Orito,Hatakeyama,Takeo,Suginome
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p. 1357 - 1358
(2007/10/02)
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- A facile preparation of sulphoxides by the bentonite-assisted oxidation of sulphides with magnesium monoperoxyphthalate in an aprotic solvent
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The title oxidation has been investigated in acetonitrile. The substrates examined include alkyl aryl, diaryl, dialkyl, and cyclic sulphides, which afforded the corresponding sulphoxides in good to excellent yields under neutral and mild conditions.
- Hirano,Ueno,Morimoto
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p. 3125 - 3134
(2007/10/02)
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- Zeolite-Assisted Oxidation of Sulfides with Sodium Bromine Trihydrate in Aprotic Solvents
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The title oxidation of a variety of sulfides was effectively performed in dichloromethane in the presence of H+-exchanged zeolite F-9, affording the corresponding sulfoxides in good yields under mild and neutral conditions.
- Hirano, Masao,Kudo, Hiroyuki,Morimoto, Takashi
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p. 1492 - 1494
(2007/10/02)
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- A Facile Synthesis of Sulfoxides by Oxidation of Sulfides with Sodium Bromite in an Aprotic Solvent in the Presence of Clay Minerals
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The title oxidation has been performed in dichloromethane in the presence of "wet"-montmorillonite and -kaolin.The substrates studied include dialkyl, alkyl aryl, diaryl, and cyclic sulfides, which give the corresponding sulfoxides in good yields under ne
- Hirano, Masao,Kudo, Hiroyuki,Morimoto, Takashi
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p. 1744 - 1746
(2007/10/02)
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- Oxygen Exchange between Sulphoxides and Sulphides. Part 3. The HCl-Catalysed Reduction of Aryl Methyl Sulphoxides by Dialkyl Sulphides in Aqueous Methanol
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Dialkyl sulphides reduce aryl methyl sulphoxides in aqueous methanol in the presence of ca. 4 mol dm-3 HCl.Ring substitution in phenyl methyl sulphoxides moderately affects their reactivity towards dibutyl sulphide, the overall effect resulting in a Hammett ρ value of -1.6.This parameter is a measure of the effect of structural changes on a protonation pre-equilibrium, the formation of chlorosulphonium ion, and its subsequent partitioning between reduction and return to reactants by the action of water.Changing the alkyl moiety of the sulphides induces moderate reactivity changes suggesting a compensation of opposite polar and steric effects.Sulphoxides with electron-releasing groups display the highest selectivity towards dialkyl sulphides.When a large concentration of sulphide is used, both racemization of chiral sulphoxide and 18O exchange with the aqueous solvent are suppressed and this suggests that the species ArR1SCl+ is a common intermediate for these processes and for the reduction reaction.These and other kinetic findings indicate that the reduction step involves the displacement at the ArR1SCl+ chlorine of a sulphide by a sulphide molecule rather than by chloride ion and rules out, for the racemization too, the hypothesis involving a free halogen intermediate.
- Miotti, Umberto
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p. 617 - 622
(2007/10/02)
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- Mechanism of the Oxidation of Sulphides with Sodium Periodate
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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
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p. 683 - 688
(2007/10/02)
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- Selective Oxidation of Sulphides and Disulphides
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Monoperphthalic acid has been found to be very efficient and convenient reagent for the oxidation of a variety of dialkylsulphides and dialkyl disulphides yielding sulphoxides and thiosulphinates respectively.Thiosulphinates have been prepared selectively
- Rajanikanth, B.,Ravindranath, B.
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p. 877 - 878
(2007/10/02)
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- Mechanism of the Reaction of Dialkyl Sulphides with Bromamine T in Alkaline Medium
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Bromamine T (p-MeC6H4SO2NBr-K+) reacts readily with dialkyl sulphides (R2S) to yield sulphoxides (R2SO) and sulphimides (R2SNTs).The kinetics of the reaction were investigated in buffered alkaline water-methanol solutions.In rate-determining steps HOBr and p-MeC6H4SO2NHBr formed in equilibrium reactions convert dialkyl sulphides into bromosulphonium (R2SBr+) intermediates (ρ* -1.22 and 1.11, ρI -13.3 and -14.4, respectively.).Electrophilic additions of Br+ to sulphur atom are significantly hindered by the steric effect of S-alkyl groups (δ 0.713 and 0.765, ρs 0.766 and 0.792, respectively).Products are rapidly formed from bromosulphonium ions by nucleophilic displacement with OH- and p-MeC6H4SO2NH- nucleophiles.Product distribution depends on pH and the concentration of p-MeC6H4SO2NH2 but is not influenced markedly by S-alkyl groups in sulphides.Results are compared with those obtained earlier for chloramine T.
- Ruff, Ferenc,Kucsman Arpad
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p. 1075 - 1080
(2007/10/02)
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