- A very simple method for the preparation of symmetrical disulfides
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Addition of sulfuryl chloride to an alkyl- or arylthiol in a 1:2 ratio under solvent free conditions or in CH2Cl2 solution produces the corresponding disulfides in nearly quantitative yields. A serendipitiously discovered, extremely simple, fast and previously unreported method for the preparation of symmetrical aliphatic, aromatic and heteroaromatic disulfides is reported. Addition of sulfuryl chloride to an alkyl- or arylthiol in a 1:2 ratio under solvent free conditions or in dichloromethane solution produces the corresponding disulfides in nearly quantitative yields with the concomitant elimination of gaseous SO2 and 2 equiv of HCl. Thus, optimally the reaction needs no work-up at all leaving the disulfide as the sole product in excellent yield. In dichloromethane solution, the reaction is conveniently carried out in a rotary evaporator by mixing the solvent, thiol and SO2Cl2 in a round-bottomed flask followed by evaporation of the volatiles.
- Leino, Reko,L?nnqvist, Jan-Erik
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- Oxidative dehydrogenation of thiols to disulfides at room temperature using silica supported iron oxide as an efficient solid catalyst
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Selective transformation of thiols to disulfides by means of oxidative dehydrogenation has been described using silica supported iron oxide under base- and solvent-free reaction conditions at room temperature in an open atmosphere. The easiness of catalyst preparation, green reaction conditions, easy separation of the formed products and catalyst from the reaction mixture, and recyclability of the catalyst, are the most attractive facets of our synthetic procedure which, being ecofriendly, will find immense applications in academic and industrial sectors.
- Paul, Susmita,Islam
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- Iron(III)-Ethylenediaminetetraacetic Acid Mediated Oxidation of Thiols to Disulfides with Molecular Oxygen
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FeIIIEDTA in aqueous methanol offers a simple environmentally acceptable synthetic tool for oxidizing thiols to the corresponding disulfides by molecular oxygen in excellent yields, under mild conditions and devoid of side reactions.
- Rao, Tumula Venkateshwar,Sain, Bir,Murthy, Pappu S.,Prasada Rao, Turaga S. R.,Jain, Ajay K.,Joshi, Girish C.
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- Silica-supported ICl as a novel heterogeneous system for the rapid and selective oxidation of thiols to symmetrical disulfides
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ICl-SiO2 as a new reactive system was prepared by treatment of iodine monochloride with activated silica gel in chloroform. ICl-SiO2 in a heterogeneous system efficiently converted thiols to the corresponding disulfides under mild conditions in high yields at room temperature.[image omitted].
- Karami, Bahador,Farahi, Mahnaz,Montazerozohori, Morteza,Nasr-Esfahani, Masoud
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- Simple and green method for synthesis of symmetrical dialkyl disulfides and trisulfides from alkyl halides in water; PMOxT as a sulfur donor
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An environmentally new, mild and efficient method has been developed for the synthesis of dialkyl disulfides and dialkyl trisulfides in aqueous conditions by a reaction between alkyl halides (and tosylate) and potassium-5-methyl-1,3,4-oxadiazole-2-thiolate (PMOxT) as a sulfur transfer reagent. The advantages of this method are that it occurs under mild reaction conditions, it is base free, it uses water as the solvent and it occurs in high yields. A variety of dialkyl disulfides and dialkyl trisulfides can be obtained in good to excellent yields up to 98%.
- Soleiman-Beigi, Mohammad,Mohammadi, Fariba
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- Preparation and characterization of long-chain di-n-alkyl disulfides
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The preparation of long-chain symmetric di-n-alkyl disulfides based on the reaction of BUNTE SALTS (RS2O3Na) with iodine is reported. 1H-NMR, FT-IR, and FT-RAMAN spectra of the solid and liquid/molten aliphatic title disulfides were recorded. An assignment of the vibrational frequencies is proposed especially in regard to the S-S and C-S vibrations. Distinct spectral differences are determined between the solid and liquid state, as well as between disulfides with even and those with odd numbered alkyl substituents, respectively. The observed phenomena are ascribed to different species in the solids and liquids/melts and their respective VAN DER WAALS interactions. In addition, mass spectra, GC-MS studies, as well as the thermal behaviour of the disulfides, based on investigations by DSC and TGA, are reported.
- Steinfatt, Ingeborg,Hoffmann, Gerhard G.,Brouwer, Ludwig,Menzel, Frank,Brockner, Wolfgang
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- Application of ionic liquids for extraction and synthesis of organosulfur compounds
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We consider the possible application of pyridinium ionic liquids to desulfurize hydrocarbon raw products and to transform the extracted toxic admixtures into promising sulfur compounds. Anodic oxidation of the extracted thiols as well as oxidation in the presence of electron mediators (N,N,N′,N′-tetramethyl-1,4-phenylenediamine, tri-p-bromophenylamine, and tri-p-tolylamine) leads to the corresponding disulfides.
- Okhlobystina,Okhlobystin,Koldaeva,Movchan,Litvin,Berberova
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- Substituted o-Aminophenols as Redox-Mediators in the Thiol Oxidation to Unsymmetrical Disulfides
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A number of substituted o-aminophenols has been investigated as redox mediators of the thiol oxidation to disulfides. The electrooxidation of o-aminophenols leads to the corresponding o-iminobenzoquinones. These compounds react with thiols in the solution with a formation of disulfides. It was established that the use of 4,6-di-tert-butyl-2-(tert-butylamino)phenol as a redox mediator can reduce the overpotential of the thiol oxidation by 0.2-1.4 V depending on the nature of the coupling thiols. The unsymmetrical disulfides with alkyl, aryl, and heteroaryl substituents were obtained as the result of the indirect electrosynthesis.
- Berberova, Nadezhda T.,Burmistrova, Daria A.,Galustyan, Andrey,Smolyaninov, Ivan V.
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- Symmetrical disulfide synthesis via nickel-catalysis using potassium sulfide as sulfur source
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Abstract: An efficient one-pot method for the synthesis of organic disulfides from aryl and alkyl halides and potassium sulfide has been described. K2S acts as an inexpensive and readily available sulfur source. A variety of symmetric diaryl and dialkyl disulfides was prepared in good to excellent yields using NiCl2·6H2O and acetylacetone as the catalytic system. Graphical abstract: [Figure not available: see fulltext.]
- Soleiman-Beigi, Mohammad,Arzehgar, Zeinab
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p. 1759 - 1763
(2016/09/28)
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- Dithiooxamide as an Effective Sulfur Surrogate for Odorless High-Yielding Carbon-Sulfur Bond Formation in Wet PEG200 as an Eco-Friendly, Safe, and Recoverable Solvent
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In this study, we have employed dithiooxamide, a solid, odorless, and commercially available compound, as a sulfur surrogate for the preparation of dialkyl sulfides from available alkyl halides in high yields. This sulfur transfer agent was also used for a copper-catalyzed high-yielding preparation of diaryl sulfides from their available aryl halides and for the preparation of thia-Michael adducts in high yields. All the reactions were performed under odorless conditions in wet PEG200 (PEG = polyethylene glycol), which is an eco-friendly, safe, and recoverable solvent. The protocols were easily applicable to large-scale operation.
- Firouzabadi, Habib,Iranpoor, Nasser,Gorginpour, Forough,Samadi, Arash
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supporting information
p. 2914 - 2920
(2015/05/04)
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- An efficient one-pot method for the direct synthesis of organic disulfides from aryl/alkyl halides in the presence of CuCl using morpholin-4-ium morpholine-4-carbo-dithioate
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A novel and expedient route is described for the one-pot synthesis of symmetric diaryl (dialkyl) disulfides derivatives via morpholin-4-ium morpholine-4-carbo-dithioate and aryl (alkyl) halides reactions in the presence of CuCl in an aqueous solvent system. Morpholin-4-ium morpholine-4-carbo-dithioate used as new solid, stable and easy handle sulfur Sourcage.
- Soleiman-Beigi, Mohammad,Arzehgar, Zeinab
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p. 395 - 402
(2015/06/22)
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- Oxidation of thiols using K2S2O8 in ionic liquid
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A green, straightforward, and novel method for oxidation of thiols to the corresponding disulfides is reported using K2S2O8 in the ionic liquid 1-butyl-3-methylimidazolium bromide [(bmim)Br] at 65-70C. The corresponding disulfides were obtained in excellent yield and short reaction time.
- Hajipour, Abdol R.,Mostafavi, Majid,Ruoho, Arnold E.
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experimental part
p. 1920 - 1923
(2010/02/28)
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- A novel reduction of sodium alkyl thiosulfates with InCl 3(cat.)/Sm(0) system in aqueous media: Facile synthesis of disulfides
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A novel reduction of sodium alkyl thiosulfates. with InCl 3(cat.)/Sm(0) system in aqueous media has been developed, which generates the corresponding disulfides in good yields.
- Li, Pinhua,Wang, Lei,Yang, Yaner,Sun, Xinhua,Wang, Min,Yan, Jincan
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p. 376 - 379
(2007/10/03)
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- Oxidation of thiols with 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate (BABOD) under non-aqueous conditions
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The preparation of 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate and the use of this reagent for selective oxidation of aromatic and aliphatic thiols to their corresponding disulfides under non-aqueous conditions is reported.
- Hajipoura,Bagheri, Hamid,Ruoho, Arnold E.
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p. 286 - 287
(2007/10/03)
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- Oxidation of thiols to the corresponding symmetric disulfides with benzyltriphenylphosphonium peroxodisulfate (BTPPD) under nonaqueous conditions
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This article describes the preparation of benzyltriphenylphosphonium peroxodisulfate (BTPPD), an efficient and mild reagent for oxidation of a variety of aromatic and aliphatic thiols to the corresponding disulfides in refluxing acetonitrile. The experimental procedure is simple and the products are easily isolated in excellent yields.
- Hajipour, Abdol R.,Ruoho, Arnold E.
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p. 1277 - 1281
(2007/10/03)
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- A novel reduction of sodium alkyl thiosulfates using samarium metal without an activating agent in water
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A novel metallic samarium promoted reduction of sodium alkyl thiosulfates in the absence of an activating agent occurs to afford the corresponding disulfides with good yields in water at 90°C.
- Wang, Lei,Li, Pinhua,Zhou, Li
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p. 8141 - 8143
(2007/10/03)
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- Oxidation of thiols to the corresponding disulfides with tetramethylammonium chlorochromate under non-aqueous conditions
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This paper describes the preparation of tetramethylammonium chlorochromate (TMACC) as an efficient and mild reagent for oxidation in refluxing acetonitrile of a variety of aromatic and aliphatic thiols, giving the corresponding disulfides; the experimental procedure is simple, and the products are easily isolated in excellent yields.
- Hajipour, Abdol R.,Ruoho, Arnold E.
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p. 547 - 549
(2007/10/03)
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- Cobalt phthalocyanine mediated aerobic oxidation of thiols: A simple and convenient preparation of disulphides
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Cobalt phthalocyaninetetrasulphonamide/tetrasodium salt of cobalt tetrasulphophthalocyanine catalyzed oxidation with molecular oxygen form a simple, efficient and environmentally acceptable synthetic tool for the oxidation of thiols to disulphides in excellent yields, under mild conditions and without any side reactions.
- Venkateshwar Rao,Narasimha Rao,Jain, Suman L.,Sain, Bir
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p. 1151 - 1157
(2007/10/03)
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- Water accelerated Sm/TMSCl reductive system: Debromination of vic- dibromides and reduction of sodium alkyl thiosulfates
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A simple and efficient method for the debromination of vic-dibromides to (E)-alkenes and reduction of sodium alkyl thiosulfates to disulfides promoted by Sm/TMSCl/H2O (trace) has been described.
- Xu, Xiaoliang,Lu, Ping,Zhang, Yongmin
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p. 1917 - 1925
(2007/10/03)
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- Preparation of dialkyl disulfides via reduction of alkylthiocyanates with TiCl4/Sm system
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Dialkyl disulfides can be readily prepared in moderate to good yields via reduction of alkylthiocyanates with TiCl4/Sm system in THF at 0°C.
- Guo, Hongyun,Zhan, Zhuangping,Zhang, Yongmin
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p. 2721 - 2724
(2007/10/03)
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- Preparation of disulfides by reduction of sodium alkyl thiosulfates with metallic samarium and catalytic amount of iodine
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Sm/I2 reduces sodium alkyl thiosulfates to the corresponding disulfides in good to excellent yields in THF at room temperature.
- Huang, You,Zhang, Yongmin,Wang, Yulu
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p. 1043 - 1047
(2007/10/03)
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- Preparation of disulfides by the oxidation of thiols using bromine
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Medium length aliphatic disulfides are easily synthesized via the bromine-oxidation of thiols in the absence of solvent. Bromine can also oxidize long aliphatic and aromatic thiols to disulfides in solution. All yields are quantitative.
- Wu, Xiaoming,Rieke, Reuben D.,Zhu, Lishan
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p. 191 - 196
(2007/10/03)
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- Reductive cleavage of C - S bond by samarium diiodide: A novel method for the synthesis of disulfides and thiolesters
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Disulfides were obtained by the reaction of thiocyanates with equivalent SmI2. Smarium thiolates were generated by the reaction of an equivalent of thiocyanates with two equivalents of SmI2, and then reacted smoothly with acyl chlorides to give thiolesters.
- Jia, Xueshun,Zhang, Yongmin,Zhou, Zunjun
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p. 8833 - 8834
(2007/10/02)
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- Reductive cleavage of S-S bond by samarium diiodide: A novel method for the synthesis of disulfides
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Samarium diiodide reductively cleaves the S-S bond of sodium alkyl thiosulfates to give the corresponding disulfides in moderate to good yields under mild and neutral conditions.
- Jia,Zhang,Zhou
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p. 2893 - 2898
(2007/10/02)
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- Formation of Thiocarbonyl Compounds in the Reaction of Ebselen Oxide with Thiols
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Reaction of α-toluenethiol with Ebselen oxide, 2, affords dibenzyl disulfide and seleno sulfide 5, R = PhCH2.In the course of this reaction, thiobenzaldehyde is formed and can be trapped with cyclopentadiene in 90percent yield.Reaction of 2-propene-1-thiol with 2 afforded thioacrolein dimer in 69percent yield and seleno sulfide 5, R = CH2-CH=CH2.Trapping, stereochemical, and isotopic exchange studies were used to determine if in the reaction of 2 with 1-heptanethiol, cyclohexanethiol, and N-acetyl-D,L-cysteine thiocarbonyl compounds heptanethial, cyclohexanethione, and 2-acetamino-3-thioxopropanoic acid (α-thioformyl-N-acetylglycine), respectively, are also formed.These studies showed that free thiocarbonyl compounds are not formed in these reactions.
- Glass, Richard S.,Farooqui, Firdous,Sabahi, Mahmood,Ehler, Kenneth W.
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p. 1092 - 1097
(2007/10/02)
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- Oxidation of Thiols by Nitric Oxide and Nitrogen Dioxide: Synthetic Utility and Toxicological Implications
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Thiols are readily oxidized to disulfides by either nitric oxide or nitrogen dioxide.Reaction conditions are mild, and quantitative yields can be obtained.The reactions are useful for preparative purposes and may have toxicological significance.
- Pryor, William A.,Church, Daniel F.,Govindan, C. K.,Crank, George
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p. 156 - 159
(2007/10/02)
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- Desulfuration Using Plasma Techniques, III. - Reaction of Thioethers
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Plasma desulfurations were tested with nine thioethers.While aliphatic, as well as aromatic thioethers and thiophene react easily, benzothiophenes are hard to desulfurize.Predominant reaction products are low molecular alkenes and alkanes (Table 1).Addition of oxygen greatly improves the results (Table 2).
- Suhr, Harald,Henne, Peter,Iacocca, Diodoro,Ropero, Marcos J.
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p. 441 - 446
(2007/10/02)
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