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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 16
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Original Articles

An Environmentally Friendly Oxidation of Thiols to Disulfides by Calcium Hypochlorite and Montmorillonite K10 in Hexane

Masao Hirano Department of Applied Chemistry, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184, Japan
,
Shigetaka Yakabe Department of Applied Chemistry, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184, Japan
,
Masataka Fukami Department of Applied Chemistry, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184, Japan
&
Takashi Morimoto Department of Applied Chemistry, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184, Japan
Pages 2783-2788 | Received 23 Feb 1997, Published online: 22 Aug 2006

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Samad Shoghpour Bayraq, Ahmad Nikseresht & Iman Khosravi. (2013) (NH4)6Mo7O24·4H2O as an Efficient, Selective, and Reusable Catalyst for the Oxidation of Thiols to Disulfides Using Potassium Bromate. Phosphorus, Sulfur, and Silicon and the Related Elements 188:9, pages 1236-1243.
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DaianeM.L. Cabrera, FrancieliM. Líbero, Diego Alves, Gelson Perin, EderJ. Lenardão & RaquelG. Jacob. (2012) Glycerol as a recyclable solvent in a microwave-assisted synthesis of disulfides. Green Chemistry Letters and Reviews 5:3, pages 329-336.
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Pankaj Attri, Shweta Gupta & Rupesh Kumar. (2012) Green methodology for the preparation of disulfide. Green Chemistry Letters and Reviews 5:1, pages 33-42.
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W. Marjit Singh & JubarajB. Baruah. (2008) Rosolic Acid–Catalyzed Conversion of Thiols to Disulfides. Synthetic Communications 39:2, pages 325-331.
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Abdol R. Hajipour, Somayeh Safai & Arnold E. Ruoho. (2006) Oxidation of thiols with methyltriphenylphosphonium dichromate (MTPPD) in dichloromethane at room temperature. Journal of Sulfur Chemistry 27:5, pages 441-444.
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M. Joshaghani , A.R. Khosropour, H. Jafary & I. Mohammadpoor-Baltork. (2005) Mild and Highly Efficient Preparation of Symmetrical Disulfides and Diselenides Using Bipyridinum Hydrobromide Perbromide as a New Oxidative Reagent. Phosphorus, Sulfur, and Silicon and the Related Elements 180:1, pages 117-123.
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Iraj Mohammadpoor-Baltork, Hamid Reza Memarian & Kiumars Bahrami. (2004) SELECTIVE AND CONVENIENT OXIDATION OF THIOLS TO DISULFIDES USING n-BUTYLTRIPHENYLPHOSPHONIUM DICHROMATE (Bu PPh3)2Cr2O7 IN SOLUTION, UNDER SOLVENT-FREE CONDITIONS AND MICROWAVE IRRADIATION. Phosphorus, Sulfur, and Silicon and the Related Elements 179:11, pages 2315-2321.
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Fen-Er Chen, Yun-Wen Lu, Yan-Ping He, You-Fu Luo & Ming-Guo Yan. (2002) TETRABUTYLAMMONIUM PEROXYDISULFATE IN ORGANIC SYNTHESIS. XII.[1] A CONVENIENT AND PRACTICAL PROCEDURE FOR THE SELECTIVE OXIDATION OF THIOLS TO DISULFIDES WITH TETRABUTYLAMMONIUM PEROXYDISULFATE UNDER SOLVENT-FREE CONDITIONS. Synthetic Communications 32:22, pages 3487-3492.
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B. Movassagh, M.M. Lakouraj & K. Ghodrati. (1999) Caro's Acid Supported on Silica Gel. Part 1: Oxidative Coupling of Thiols to Disulfides. Synthetic Communications 29:20, pages 3597-3603.
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Shigetaka Yakabe, Masao Hirano & Takashi Morimoto. (1998) vic-Dichlorination of Olefins with Sodium Chlorite, Mn(acac)3, and Moist Alumina in Dichloromethane. Synthetic Communications 28:10, pages 1871-1878.
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Masao Hirano, Hiroyuki Monobe, Shigetaka Yakabe & Takashi Morimoto. (1998) Nuclear Monobromination of Alkyl Phenyl Ethers with NaClO2, NaBr, Mn(acac)3, and Moist Silica Gel in Aprotic Solvent. Synthetic Communications 28:8, pages 1463-1470.
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Masao Hirano, Shigetaka Yakabe, Hiroyuki Monobe & Takashi Morimoto. (1998) Regioselective Aromatic Monobromination of Alkyl Phenyl Ethers with NaClO2, NaBr, Mn(acac)3, and Montmorillonite K10 in Dichloromethane. Synthetic Communications 28:4, pages 669-676.
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Articles from other publishers (15)

Hamid Mahmoudi, Abdollah Salimi & Amin Rostami. (2023) Selective indirect electrochemical oxidation of sulfides and thiols using DDQ as an efficient and cost-effective electrocatalyst. Tetrahedron Letters 117, pages 154368.
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Mastaneh Shariati, Amin Rostami, Gholamhassan Imanzadeh & Somayyeh Kheirjou. (2018) Enzymatic regeneration of DDQ in aerobic oxidation of sulfides and oxidative coupling of thiols: New bioinspired cooperative catalytic system. Molecular Catalysis 461, pages 48-53.
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Donya Khaledian, Amin Rostami & Seyed Amir Zarei. (2018) Laccase-catalyzed in situ generation and regeneration of N-phenyltriazolinedione for the aerobic oxidative homo-coupling of thiols to disulfides. Catalysis Communications 114, pages 75-78.
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Jing Chen, Cheng-Shi Jiang, Wen-Quan Ma, Li-Xin Gao, Jing-Xu Gong, Jing-Ya Li, Jia Li & Yue-Wei Guo. (2013) The first synthesis of natural disulfide bruguiesulfurol and biological evaluation of its derivatives as a novel scaffold for PTP1B inhibitors. Bioorganic & Medicinal Chemistry Letters 23:18, pages 5061-5065.
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Yunyun Liu, Hang Wang, Chunping Wang, Jie-Ping Wan & Chengping Wen. (2013) Bio-based green solvent mediated disulfide synthesis via thiol couplings free of catalyst and additive. RSC Advances 3:44, pages 21369.
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Samuel Thurow, Vanda A. Pereira, Débora M. Martinez, Diego Alves, Gelson Perin, Raquel G. Jacob & Eder J. Lenardão. (2011) Base-free oxidation of thiols to disulfides using selenium ionic liquid. Tetrahedron Letters 52:5, pages 640-643.
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Hadi ADIBI, Heshmat Allah SAMIMI & Nasser IRANPOOR. (2008) Iron(III) Trifluoroacetate: Chemoselective and Recyclable Lewis Acid Catalyst for Diacetylation of Aldehydes, Thioacetalization and Transthioacetalization of Carbonyl Compounds and Aerobic Coupling of Thiols. Chinese Journal of Chemistry 26:11, pages 2086-2092.
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Eder J. Lenardão, Renata G. Lara, Márcio S. Silva, Raquel G. Jacob & Gelson Perin. (2007) Clean and fast oxidative transformation of thiols to disulfides under solvent-free conditions. Tetrahedron Letters 48:43, pages 7668-7670.
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Amit Saxena, Ajeet Kumar & Subho Mozumdar. (2007) Ni-nanoparticles: An efficient green catalyst for chemo-selective oxidative coupling of thiols. Journal of Molecular Catalysis A: Chemical 269:1-2, pages 35-40.
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Jing-Xu Gong, Xu Shen, Li-Gong Yao, Hualiang Jiang, Karsten Krohn & Yue-Wei Guo. (2007) Total Synthesis of Gymnorrhizol, an Unprecedented 15-Membered Macrocyclic Polydisulfide from the Chinese Mangrove Bruguiera gymnorrhiza . Organic Letters 9:9, pages 1715-1716.
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I. V. Koval’. (2007) Reactions of thiols. Russian Journal of Organic Chemistry 43:3, pages 319-346.
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Behzad Zeynizadeh & Nasser Iranpoor. (2013) Oxidative Coupling of Thiols to Disulfides with Ti(IV) in the Presence of NaI under Air Atmosphere. Journal of the Chinese Chemical Society 50:4, pages 849-852.
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Behzad Zeynizadeh. (2019) Oxidative Coupling of Thiols to Disulfides with Iodine in Wet Acetonitrile. Journal of Chemical Research 2002:11, pages 564-566.
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Mohammad Ali Zolfigol. (2001) Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions. Tetrahedron 57:46, pages 9509-9511.
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M. HIRANO, S. YAKABE, M. FUKAMI & T. MORIMOTO. (2010) ChemInform Abstract: An Environmentally Friendly Oxidation of Thiols to Disulfides by Calcium Hypochlorite and Montmorillonite K10 in Hexane.. ChemInform 28:42, pages no-no.
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