- Synthesis and characterization of task-specific ionic liquids based on peroxydisulfate and their application in oxidation reactions
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Four new task-specific ionic liquids based on the peroxydisulfate ion were synthesized by the ion exchange method and characterized by FTIR and 1H NMR spectroscopy and elemental analysis. The physicochemical characteristics of these ionic liquids such as density, thermal, stability, conductivity, viscosity, and solubility in common solvents have been investigated in detail. The experimental results testify that the ionic liquids prepared show excellent performance as both oxidant and medium in given oxidation reactions of alcohols and thiols under mild reaction conditions.
- Shi, Shenyi,Kong, Aiguo,Zhao, Xinhua,Zhang, Qiying,Shan, Yongkui
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- Oxidation of organic compounds by potassium permanganate supported on montmorillonite K10
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The oxidation of organic compounds by potassium permanganate supported on Montmorillonite K10 has been studied under solvent-free conditions and the results compared with those from corresponding reactions where the reductants are dissolved in methylene chloride. Under both sets of conditions, primary benzylic and secondary alcohols are converted to aldehydes and ketones respectively, sulfides are oxidized to sulfones, and thiols undergo oxidative coupling to give disulfides. Surprisingly, reaction times under solvent-free conditions are shorter than those observed when the reductants are dissolved in a solvent.
- Shaabani, Ahmad,Bazgir, Ayoob,Lee, Donald G.
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- Potassium permanganate oxidation of organic compounds
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It has been discovered that potassium permanganate is an effective heterogeneous oxidant, even without resorting to the use of a solid support, if acetonitrile is employed as the solvent. Primary benzylic and secondary alcohols are converted to the corresponding aldehydes and ketones, alkyl arenes are oxidized to the corresponding α-ketones in good yields using this procedure, and both alkyl and aryl sulfides are smoothly converted to the corresponding sulfones, also in excellent yields. When methylene chloride is used as the solvent, instead of acetonitile, the yields of aldehydes, ketones, α-ketones, and sulfones are reduced. However, the oxidation of thiols to disulfides proceeds satisfactorily when methylene chloride is the solvent.
- Shaabani, Ahmad,Tavasoli-Rad, Farahnaz,Lee, Donald G.
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- CHEMISTRY OF A MOLYBDENUM-PERSULFIDE COMPLEX: ALKYLATION AND OXIDATIVE COUPLING
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The reaction of alkyl halides, sulfinyl and sulfonyl chlorides with (NH4)2 has been found to afford sulfides and disulfides in good-excellent yield.The effect of solvent polarity and reaction time is discussed.
- Harpp, David N.,MacDonald, J. Gavin
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- Heteroaromatic azo compounds as efficient and recyclable reagents for direct conversion of aliphatic alcohols into symmetrical disulfides
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4,4′-Azopyridine 1a and 5,5′-dimethyl-3,3′-azoisooxazole 1e are used for the efficient, direct, and selective conversion of aliphatic alcohols into their corresponding disulfides in high yields under Mitsunobu conditions in combination with PPh3/sub
- Iranpoor, Nasser,Firouzabadi, Habib,Khalili, Dariush
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- Microwave assisted oxidative coupling of thiols to symmetrical disulfides with tripropylammonium fluorochromate(VI) (TPAFC)
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Tripropylammonium fluorochromate(VI) (TPAFC) is an efficient and novel reagent, which can be prepared easily and oxidizes thiols to the corresponding disulfides, quickly. The reactions are performed cleanly and are controlled to stop at the disulfide stage, without over-oxidation or side products. Coupling of thiols to their corresponding disulfides, was studied in solution at room temperature and under conditions using a minimal amount of solvent under microwave irradiation. The easy procedure, simple work-up, short reaction times, and excellent yields are other advantages of this reagent.
- Mohammadi, Mohammad Kazem,Ghammamy, Shahriare
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- Tributylammonium halochromates/silica gel: Simple reagents for oxidative coupling of thiols to symmetrical disulfides
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New orange solid tributylammonium halochromates, (C4H 9)3N+CrO3X-, TBAXC (X=F, Cl) are easily synthesized by the reaction of tributylammonium fluoride and chloride with CrO3 in a 1:1 molar ratio in the presence of HF and HCl. Tributylammonium halochromates(VI) are versatile reagent for the effective and selective oxidation of organic substrates. Silica gel supported TBAFC and TBACC are versatile reagents for the effective and selective oxidation of organic substrates, in particular, thiols, under mild conditions. Considerable improvements are observed in the presence of the absorbent, making the work-up much more convenient. New orange solid tributylammonium halochromates, (C 4H9)3N+CrO3X -, TBAXC (X=F, Cl) are easily synthesized by the reaction of tributylammonium fluoride and chloride with CrO3 in a 1:1 molar ratio in the presence of HF and HCl. Tributylammonium halochromates(VI) are versatile reagent for the effective and selective oxidation of organic substrates. Copyright
- Mohammadi, Mohammad Kazem,Ghammamy, Shahriare,Zarrinabadi, Soroush,Farjam, Mohammad Hossein,Sabayan, Behrang
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- Oxidative coupling of thiols to disulfides using a solid anhydrous potassium phosphate catalyst
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Thiols are oxidized to the corresponding disulfides with a mild base, anhydrous potassium phosphate, under ambient conditions in the presence of air.
- Joshi, Ashutosh V.,Bhusare, Sudhakar,Baidossi, Mubeen,Qafisheh, Nida,Sasson, Yoel
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- Ethylenebis(N-methylimidazolium) chlorochromate (EBMICC): An efficient and selective reagent for the oxidation of thiols to disulfides
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Ethylenebis(N-methylimidazolium) chlorochromate was prepared by addition of N-methylimidazole to 1,2-dibromoethane to form the corresponding dibromide salt and subsequent treatment of this salt with CrO3 in 6N HCl solution. It is a stable yellow-orange solid, which oxidized thiols to the corresponding disulfides at room temperature. Selective oxidation of thiols in the presence of sulfides and hydroxyl groups was also achieved with this reagent.
- Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Khaledi, Hamid,Ghodrati, Keivan
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- Homolytic and conjugate addition of thiols to 2,4-Dimethyl-2-vinyl-1,3-dioxa-2-silacyclohexane
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Homolytic reaction of 1-propane-and 1-pentanethiols to 2,4-dimethyl-2-vinyl-1,3-dioxa-2-silacyclohexane, initiated by di-tert-butyl peroxide at 130°C, yields a mixture of isomeric sulfides (95%) as a result of addition at the α-and β-positions of the vinyl group. Conjugate addition of alkanethiols in the presence of the corresponding sodium thiolate at 100°C gives 10% of the same α-and β-regioisomeric sulfides at a ratio of 1:20.
- Makaeva,Zorin,Musavirov,Brod'ko,Gvozdik,Musavirov
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- TWO SULFUR CONSTITUENTS FROM ALLIUM SCHOENOPRASUM
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Two kinds of disulfide has been isolated from Allium schoenoprasum and their structures established as methyl pentyl disulfide and pentyl hydrodisulfide by spectroscopic and synthetic methods.These compounds, which smell like sweet onions, are important aroma constituents. Key Word Index - Allium schoenoprasum; Alliaceae; steam volatile oil; methyl pentyl disulfide; pentyl hydrodisulfide.
- Kameoka, Hiromu,Hashimoto, Seiji
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- Redox chemistry between graphene oxide and mercaptan
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We report here redox reactions between graphene oxide (GO) and mercaptans, which reduces GO to reduced graphene oxide (RGO) and oxidizes mercaptans into disulfides. The reduction processes of GO using various mercaptans as the reducing agents are investigated through XPS, TGA, FT-IR, Raman and EA analysis. The degree of reduction of RGO depends on molecular structure of mercaptans and is controlled by the reaction time. The redox reaction is also employed to oxidize mercaptans into disulfides in medium to high yields under moderate conditions. The mechanism of the redox reaction may involve nucleophilic ring opening of oxirane on GO by alkylthio moiety, followed by addition of another alkylthio group, leaving the resulting disulfide. The reduction of the hydroxy group could be more complex, involving both radical and anionic processes.
- Fan, Deqin,Zhang, Chao,He, Junpo,Hua, Rong,Zhang, Yang,Yang, Yuliang
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- Oxidative coupling of thiols to disulfides in solution with tripropylammonium halochromates, (C3H7) 3NH[CrO3X], (X=F, Cl) adsorbed on alumina
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A mild and efficient method for the oxidative coupling of thiols by tripropylammonium fluorochromate and tripropylammonium chlorochromate absorbed on alumina in solution is reported. Alumina absorbed tripropylammonium fluorochromate and tripropylammonium chlorochromate are efficient and new reagents, which are easily prepared and oxidize thiols to the corresponding disulfides quickly. The reactions are clean and readily controlled to stop at the disulfide stage without the formation of common over-oxidized side products. Thus the advantages of the easy procedure and work up, short reaction times, and excellent yields make this a viable alternative method.
- Hassanijoshaghani, Ali,Ghammamy, Shahriare,Bagi, Shahryar,Moghimi, Ali,Javanshir, Zahra
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- Selective and simple phase transfer catalyzed synthesis of disulfides from thiols
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Two novel methods of synthesis of disulfides from thiols or their Na salts in the phase transfer catalytic system CBr4/18-crown-6/benzene or toluene are developed and the products isolated in 67-8.8% yields.
- Abele, Edgars,Abele, Ramona,Lukevics, Edmunds
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- A simple and practical method for the oxidation of thiols to disulfides at mild conditions without solvents
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A green, straightforward, and novel method for the oxidation of thiols to the corresponding disulfides is reported using hydrogen peroxide catalyzed by tetrabutylammonium iodide (TBAI) without solvents at room temperature. The corresponding disulfides were obtained with excellent yields and short reaction times. Copyright
- He, Ying,Hang, Dongliang,Lu, Ming
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- Application of Bulky NHC-Rhodium Complexes in Efficient S-Si and S-S Bond Forming Reactions
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The efficient and straightforward syntheses of silylthioethers and disulfides are presented. The synthetic methodologies are based on new rhodium complexes containing bulky N-heterocyclic carbene (NHC) ligands that turned out to be efficient catalysts in thiol and thiol-silane coupling reactions. These green protocols, which use easily accessible reagents, allow obtaining compounds containing S-Si and S-S bonds in solvent-free conditions. Additionally, preliminary tests on coupling of mono- and octahydro-substituted spherosilicates with selected thiols have proved to be very promising and showed that these catalytic systems can be used for the synthesis of a novel class of functionalized silsesquioxane derivatives.
- Bo?t, Ma?gorzata,?ak, Patrycja
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supporting information
p. 17579 - 17585
(2021/11/18)
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- Sequential C-H activation enabled expedient delivery of polyfunctional arenes
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Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.
- Cai, Xiaoqing,Chen, Qian,Chen, Xiaojian,Gao, Yang,Huo, Yanping,Li, Xianwei,Ouyang, Wensen,Rao, Jianhang,Wang, Jie
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supporting information
p. 8075 - 8078
(2021/08/20)
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- Selective, cofactor-mediated catalytic oxidation of alkanethiols in a self-assembled cage host
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A spacious Fe(ii)-iminopyridine self-assembled cage complex can catalyze the oxidative dimerization of alkanethiols, with air as stoichiometric oxidant. The reaction is aided by selective molecular recognition of the reactants, and the active catalyst is derived from the Fe(ii) centers that provide the structural vertices of the host. The host is even capable of size-selective oxidation and can discriminate between alkanethiols of identical reactivity, based solely on size. This journal is
- Da Camara, Bryce,Dietz, Philip C.,Chalek, Kevin R.,Mueller, Leonard J.,Hooley, Richard J.
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supporting information
p. 14263 - 14266
(2020/11/24)
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- Electrochemical synthesis of organochalcogenides in aqueous medium
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The electrochemical preparation of telluride, selenide and sulfide ions was carried out in NaOH aqueous solution, using a two compartment cell. Organochalcogenides were prepared from halogenated compounds in a two-step procedure. The monochalcogenides were obtained as the major products in good yields.
- Ribeiro Neto, Pedro B.,Santana, Sonydelane O.,Levitre, Guillaume,Galdino, Danilo,Oliveira, Jadson L.,Ribeiro, Rogério T.,Barros, Maria E. S. B.,Bieber, Lothar W.,Menezes, Paulo H.,Navarro, Marcelo
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supporting information
p. 657 - 661
(2016/02/12)
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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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p. 95753 - 95759
(2016/10/22)
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- 4,4'-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea
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Heterocyclic azo compounds, prepared from corresponding amines in one step, are used as effective oxidants for the conversion of thiols into symmetrical disulfides in high yields. Among the studied azo compounds, 4,4'-azopyridine was found to be very efficient for the odorless conversion of alkyl halides into disulfides in the presence of thiourea. An attractive feature of this azo compound is that its obtained solid side product hydrazine is easily separated by filtration and can be recycled to its azo compound for further use.
- Khalili, Dariush,Iranpoor, Nasser,Firouzabadi, Habib
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p. 544 - 555
(2015/10/19)
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- A mild and efficient method for the conversion of aldehydes into nitriles and thiols into disulfides using an ionic liquid oxidant
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A simple, mild and high yielding method for the conversion of various aldehydes to nitriles has been developed using an ionic liquid reagent, hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), in combination with aqueous ammonia in CH3CN at room temperature. Moreover, the treatment of aromatic and aliphatic thiols with HMBMIBDCI resulted in the corresponding disulfides in solvent-free condition at room temperature.
- Hosseinzadeh, Rahman,Golchoubian, Hamid,Nouzarian, Mahboobe
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p. 4713 - 4725
(2015/06/30)
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- Graphene oxide (GO)-catalyzed chemoselective thioacetalization of aldehydes under solvent-free conditions
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An efficient method for the synthesis of open chain, cyclic, and unsymmetrical dithioacetals from aryl/hetero-aryl/aliphatic aldehydes is described. The reaction is performed using graphene oxide (GO) as the catalyst under solvent-free and aerobic conditions. High chemoselectivity is observed in the reaction as aryl/alkyl ketones do not give thioketals under the condition.
- Roy, Babli,Sengupta, Debasish,Basu, Basudeb
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supporting information
p. 6596 - 6600
(2015/01/08)
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- Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers
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The development of a silica-promoted highly selective synthesis of 1,2 or 1,3-dithioethers via solvent-free one-pot tandem reactions of an allyl bromide with excess thiol at room temperature is described. The choice of silica gel, either pre-calcined or moistened with water, exhibited notable regioselectivity in the formation of dithioethers. Plausible mechanistic routes were explored and postulated.
- Kundu, Samir,Roy, Babli,Basu, Basudeb
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- Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base
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An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields. The Royal Society of Chemistry 2013.
- Chatterjee, Tanmay,Ranu, Brindaban C.
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p. 10680 - 10686
(2013/09/02)
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- (NH 4) 6Mo 7O 34·4H 2O as an efficient, selective, and reusable catalyst for the oxidation of thiols to disulfides using potassium bromate
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Ammonium molybdate, (NH 4) 6Mo 7O 34·4H 2O, is found to be an efficient and selective catalyst for the oxidation of thiols to corresponding disulfides using potassium bromate in aqueous acetonitrile as the solvent. Among various solvents tested, CH3CN/H2O showed better results in terms of the reaction yield and rate. In the absence of (NH4)6Mo 7O24·4H2O, the oxidation reaction is not selective for the formation of disulfides. The catalyst can be easily recovered after completion of the reaction and reused without any significant loss of its activity. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]
- Bayraq, Samad Shoghpour,Nikseresht, Ahmad,Khosravi, Iman
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supporting information
p. 1236 - 1243
(2013/09/23)
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- Efficient ruthenium-catalysed S-S, S-Si and S-B bond forming reactions
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[RuCl(PPh3)2(3-phenylindenyl)] (1) has been shown to be an efficient catalyst in thiol dehydrogenative coupling to give disulfides. Moreover, an efficient procedure for the preparation of silylthioethers and thioboranes is presented. Complex 1 demonstrated a great ability to catalyse the coupling of thiols with silanes and boranes under mild conditions with excellent results (turnover number up to 200).
- Fernandez-Salas, Jose A.,Manzini, Simone,Nolan, Steven P.
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supporting information
p. 5829 - 5831
(2013/07/19)
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- S-Acylation of aliphatic and aromatic thiols with carboxylic acids and their esters over solid acid catalysts in the gas phase at temperatures above 200 °c
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Benzenethiol is reacted with acetic acid in a hydrogen stream over [(Mo6Cl8)Cl4(H2O) 2]·6H2O. Catalytic activity of the clusters appears above 200 °C, yielding S-phenyl thioacetate. The selectivity is 98% at 300 °C. Niobium, tantalum, and tungsten halide clusters with the same octahedral metal framework also catalyze the reaction. Benzoic acid and aliphatic carboxylic acids afford the corresponding S-phenyl carbothioates by reaction with benzenethiol. Aliphatic thiols are also S-acylated to yield the corresponding S-alkyl carbothioates. When carboxylic esters are applied to the reaction with benzenethiol over [(Nb6Cl12)Cl 2(H2O)4]·4H2O at 450 °C, the sterically unhindered moiety of the ester is incorporated into the products: S-phenyl thioacetate or methyl phenyl sulfide is obtained selectively. A Br?nsted acid site developed on the cluster complex by thermal activation is the active site of the catalyst. Hence, solid acids such as silica-alumina, zeolites, and heteropoly acids that are stable above 200 °C also catalyze these reactions.
- Nagashima, Sayoko,Yamazaki, Hitomi,Kudo, Kentaro,Kamiguchi, Satoshi,Chihara, Teiji
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p. 332 - 338
(2013/07/26)
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- The evolution of reactive ligands in the catalysis of radical processes by copper complexes
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Two radical reactions (addition of CCl4 to the double bond of oct-1-ene and oxidation of dodecane-1-thiol with air oxygen) catalyzed by copper complexes have been investigated. Various nitrogen-containing compounds (aliphatic and aromatic amines, aminoalcohols, aminoacids) were used as the ligands. In both cases, products of ligand transformation have been observed, products of the transformations have been identified by GLC-MS. In case of the CCl4 addition, the reaction can be initiated by the either copper complex or the ligand. In case of the thiol coupling, the reaction proceeds as a conjugated oxidation of both the thiol and the ligand. A correlation between the donor ability of the ligand and its reactivity has been found. Copyright Taylor and Francis Group, LLC.
- Tarkhanova,Gantman,Rostovschikova
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experimental part
p. 88 - 100
(2012/03/26)
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- Diethylamine-catalyzed dimerization of thiols: An inexpensive and green method for the synthesis of homodisulfides under aqueous conditions
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Under H2O / Et2NH / atmospheric oxygen conditions, thiols are converted to their respective homodisulfides within a few hours. The process is conducted at room temperature for quantitative dimerization of aromatic, benzylic, and aliphatic thiols without the use of any extra additive. Copyright Taylor & Francis Group, LLC.
- Abaee, M. Saeed,Mojtahedi, Mohammad M.,Navidipoor, Somayeh
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experimental part
p. 170 - 176
(2011/03/19)
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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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experimental part
p. 483 - 488
(2012/06/16)
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- Reactive ligands in radical processes catalyzed by copper complexes
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The effect of the reactivity of donor ligands on the catalytic properties of copper complexes in the oxidative dimerization of mercaptans is considered. Catalytic compositions containing metal complexes in an excess of organic reagent ligands, which can show pronounced reductive properties (aromatic amines) or, on the contrary, oxidative properties (dimethyl sulfoxide) toward substrates, exhibit the greatest activity. In the course of the oxidation of mercaptans catalyzed by copper complexes, redox reactions accompanied by not only a change in the oxidation state of the metal but also the direct interaction of a substrate with an organic donor occur. In the presence of aromatic amines, the coupled oxidation of thiols and amines occurs, whereas dimethyl sulfoxide participates in the reaction as an oxidizing agent.
- Tarkhanova,Gantman
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experimental part
p. 82 - 88
(2011/05/19)
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- An improved method for the synthesis of disulfides by periodic acid and sodium hydrogen sulfite in water
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An improved method for the synthesis of disulfide in water by using periodic acid and sodium hydrogen sulfite was developed.
- Khan, Khalid M.,Taha, Muhammad,Rahim, Fazal,Ali, Muhammad,Jamil, Waqas,Perveen, Shahnaz,Iqbal Choudhary
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experimental part
p. 415 - 419
(2011/03/22)
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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 mild and alternative approach towards symmetrical disulfides using H 3IO5/NaHSO3 combination
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Treatment of thiols with a mixture of periodic acid/sodium hydrogen sulfite gave the corresponding disulfides in good yield.
- Khan, Khalid M.,Taha, Muhammad,Ali, Muhammad,Perveen, Shahnaz
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experimental part
p. 319 - 320
(2010/04/23)
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- Carboxy pyridinium bromide perbromide reagents, part I: Selective oxidation of thiols and sulfides
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Efficient and convenient oxidation of aliphatic and aromatic thiols to disulfides and of sulfides to sulfoxides with pyridinium hydrobromide perbromide (PHBP), nicotinic acid hydrobromide perbromide (NAHBP), and 2,6-dicarboxy pyridinium hydrobromide perbromide (DCPHBP) in a solvent or under solvent free conditions and at ambient temperature is introduced. Copyright Taylor & Francis Group, LLC.
- Lakouraj, Moslem M.,Ghodrati, Keivan
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experimental part
p. 1432 - 1439
(2009/05/07)
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- Oxidation of thiols to bisulfides using silica chloride as a heterogeneous catalyst
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Silica chloride is used as a selective and effective heterogeneous catalyst for the rapid conversion of thiols to disulfides with quantitative yields in a very short period of time. Copyright
- Sathe, Manisha,Ghorpade, Ramarao,Kaushik, Mahabir Parshad
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p. 1048 - 1049
(2007/10/03)
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- Dinitrogen tetroxide impregnated charcoal (N2O 4/Charcoal): Selective oxidation of thiols to disulfides or thiosulfonates
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Selective oxidation of thiols to disulfides (RSSR) was performed by using catalytic amounts of dinitrogen tetroxide/charcoal in chloroform at r.t. while the reaction of thiols with four molar equivalents of the reagent in dichloromethane afforded thiosulfonates (RSO2SR) with excellent yields. Copyright Taylor & Francis Group, LLC.
- Iranpoor, Nasser,Firouzabadi, Habib,Pourali, Ali Reza
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p. 473 - 479
(2007/10/03)
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- A versatile one-pot synthesis of dialkyl disulfides and sulfides
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Conversions of monofluoroalkyl and alkyl bromides to the corresponding dialkyl disulfides in a one-pot synthesis using thiourea followed by basic hydrogen peroxide are described. Modified methods afford access to unsymmetrical disulfides and sulfides.
- Emerson, David W.,Bennett, Byron L.,Steinberg, Spencer M.
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p. 631 - 638
(2007/10/03)
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- Rhodium-catalyzed sulfur atom exchange reaction between organic polysulfides and sulfur
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RhH(PPh3)4 and cis-1,2-bis(diphenylphosphino)ethylene (dppv) catalyze the exchange of sulfur atoms between sulfur and organic polysulfides. The exchange of dialkyl trisulfides with sulfur proceeds at a high efficiency within 5 min at room temperature yielding a mixture of organic polysulfides.
- Arisawa, Mieko,Tanaka, Ken,Yamaguchi, Masahiko
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p. 4797 - 4800
(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 method for the syntheses of symmetrical disulfides using CsF-Celite as a solid base
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The oxidative coupling of aliphatic, aromatic and heteroaromatic thiols to disulfides using cesium fluoride-Celite is described. CsF-Celite provides an efficient, convenient and practical method for the syntheses of symmetrical disulfides.
- Shah, Syed Tasadaque A.,Khan, Khalid M.,Fecker, Miriam,Voelter, Wolfgang
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p. 6789 - 6791
(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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- Tetrabutylammonium peroxydisulfate in organic synthesis. XII. A convenient and practical procedure for the selective oxidation of thiols to disulfides with tetrabutylammonium peroxydisulfate under solvent-free conditions
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An efficient method for the oxidative coupling of thiols to their corresponding disulfide by (n-Bu4N2)S2O8 in high yields under solvent-free conditions is described. The reaction was applicable to a variety of thiols with high chemoselectivity.
- Chen, Fen-Er,Lu, Yun-Wen,He, Yan-Ping,Luo, You-Fu,Yan, Ming-Guo
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p. 3487 - 3492
(2007/10/03)
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- A rapid and efficient synthesis of symmetrical disulfides under microwave irradiation conditions
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A rapid and general method for the synthesis of symmetrical disulfides involves reaction of sulfur with sodium hydroxide under PTC-microwave irradiation condition to give sodium disulfide, which reacts with alkyl halides to afford the disulfides in good to excellent isolated yields.
- Wang, Jin-Xian,Gao, Lijuan,Huang, Danfeng
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p. 963 - 969
(2007/10/03)
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- Oxidation in fluoro alcohols: Mild and efficient preparation of disulfides from thiols
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Quantitative oxidative conversion of thiols to disulfides was effected by aqueous 30% H2O2 in trifluoroethanol at ambient temperature under neutral conditions.
- Kesavan, Venkitasamy,Bonnet-Delpon, Daniele,Begue, Jean-Pierre
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p. 223 - 225
(2007/10/03)
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- Heterogeneous permanganate oxidation of thiols
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The products that may be obtained from the oxidation of thiols by permanganate under heterogeneous conditions have been compared with those that are known to be produced by use of the same oxidant under homogeneous conditions. The products obtained from the oxidation of thiols under homogeneous and heterogeneous conditions are distinctively different. Sulfonic acids are obtained under homogeneous conditions, while disulfides are the only detectable products when the reactions are carried out heterogeneously. For example, a quantitative yield of dibutyl disulfide is obtained from the oxidation of butane-1-thiol, and oxidation of pentane-1,5- dithiol gives the corresponding cyclic disulfide, 1,2-dithiepane.
- Noureldin, Nazih A.,Caldwell, Marguerite,Hendry, Jennifer,Lee, Donald G.
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p. 1587 - 1589
(2007/10/03)
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- Preparation of dithioselenides via a selenium transfer reagent
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The addition of two moles of thiol to a unique selenium-transfer reagent, bis azole selenide 4, results in very good isolated yields of dithioselenides (RS-Se-SR).
- Ryan, M. Dominic,Harpp, David N.
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p. 8829 - 8832
(2007/10/03)
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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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p. 300 - 301
(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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