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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 10
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Original Articles

Simple, Extremely Fast, and High‐Yielding Oxidation of Thiols to Disulfides

Ashraful Alam Department of Environmental Chemistry and Materials, Faculty of Environmental Sciences and Technology, Okayama University, Okayama, JapanView further author information
,
Yutaka Takaguchi Department of Environmental Chemistry and Materials, Faculty of Environmental Sciences and Technology, Okayama University, Okayama, Japan
&
Sadao Tsuboi Department of Environmental Chemistry and Materials, Faculty of Environmental Sciences and Technology, Okayama University, Okayama, JapanCorrespondence[email protected]
Pages 1329-1333 | Received 08 Dec 2004, Published online: 16 Aug 2006

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Sauradip Chaudhuri, Hossam Zaki & Mindy Levine. (2016) Environmentally friendly procedure for the aqueous oxidation of benzyl alcohols to aldehydes with dibromodimethylhydantoin (DBDMH) and cyclodextrin: Scope and mechanistic insights. Synthetic Communications 46:7, pages 636-644.
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Kiumars Bahrami, MohammadM. Khodaei, Vida Shakibaian & Homa Targhan. (2013) Rapid and Convenient Method for the Synthesis of Symmetrical Disulfides. Phosphorus, Sulfur, and Silicon and the Related Elements 188:8, pages 981-988.
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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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Arash Ghorbani-Choghamarani, Mohammad Soleiman-Beigi & Farid Noormohammadi. (2011) Trimethylphenylammonium Tribromide as a New and Efficient Oxidizing Agent for the Oxidative Coupling of Thiols into Disulfides and Chemoselective Oxidation of Sulfides into Sulfoxides. Phosphorus, Sulfur, and Silicon and the Related Elements 186:8, pages 1665-1672.
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Arash Ghorbani-Choghamarani & Sara Sardari. (2011) Green preparation of disulfides from corresponding thiols by poly(4-vinylpyridinium nitrate) as recoverable and new polymeric reagent. Journal of Sulfur Chemistry 32:1, pages 63-69.
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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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Articles from other publishers (24)

Lin Yao, Wenjian Li, Fuhong Xiao & Guo-Jun Deng. (2023) Three-Component Tandem Amidosulfenylation of Alkenes for the Synthesis of β-Succinimide Sulfides. The Journal of Organic Chemistry.
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Mohammad Soleiman-Beigi, Mohammad Alikarami, Homa Kohzadi & Zahra Akbari. (2022) Dipotassium 1,3,4-thiadiazole-2,5-bis(thiolate) as a new S-donor for direct synthesis of symmetrical disulfides. Scientific Reports 12:1.
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赛米 乃比江·. (2022) Synthesis Study of Disulfides Promoted by Benzoyl Peroxide. Hans Journal of Chemical Engineering and Technology 12:03, pages 188-193.
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Gincy M Mathew, Aravind Madhavan, K. B. Arun, Raveendran Sindhu, Parameswaran Binod, Reeta Rani Singhania, Rajeev K Sukumaran & Ashok Pandey. (2020) Thermophilic Chitinases: Structural, Functional and Engineering Attributes for Industrial Applications. Applied Biochemistry and Biotechnology 193:1, pages 142-164.
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Caroline S. Sauer, Johannes Köckenberger & Markus R. Heinrich. (2020) Oxidative Formation of Disulfide Bonds by a Chemiluminescent 1,2-Dioxetane under Mild Conditions. The Journal of Organic Chemistry 85:14, pages 9331-9338.
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Mozafar Mohammadi, Amirhossein Sakhteman, Sajjad Ahrari, Kazem Hassanpour, Sayed Ebrahim Hashemi & Gholamreza Farnoosh. (2018) Disulfide bridge formation to increase thermostability of DFPase enzyme: A computational study. Computational Biology and Chemistry 77, pages 272-278.
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Ehsan Rezaie, Mozafar Mohammadi, Amirhossein Sakhteman, Peyman Bemani & Sajjad Ahrari. (2018) Application of molecular dynamics simulations to design a dual-purpose oligopeptide linker sequence for fusion proteins. Journal of Molecular Modeling 24:11.
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Ming Wang & Xuefeng Jiang. (2018) Sulfur–Sulfur Bond Construction. Topics in Current Chemistry 376:2.
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M. Rachèl Elzes, Niels Akeroyd, Johan F.J. Engbersen & Jos M.J. Paulusse. (2016) Disulfide-functional poly(amido amine)s with tunable degradability for gene delivery. Journal of Controlled Release 244, pages 357-365.
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Indranirekha Saikia, Arun Jyoti Borah & Prodeep Phukan. (2016) Use of Bromine and Bromo-Organic Compounds in Organic Synthesis. Chemical Reviews 116:12, pages 6837-7042.
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Zhanguo Chen, Manfei Du, Wei Xia & Junli Hu. (2016) One-pot synthesis of α,β-dehydroamino derivatives from β,β-dicyanostyrene with 1,3-dibromo-5,5-dimethylhydantoin promoted by mild base. Chemical Research in Chinese Universities 32:1, pages 68-75.
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Zhanguo Chen, Wei Xia, De'e Liu, Yali Liu, Manfei Du & Chenxi Cao. (2015) NaHCO 3 ‐Catalyzed Hihgly Regiospecific Aminobromination of ß,ß‐Dicyanostyrene Derivatives with 1,3‐Dibromo‐5,5‐dimethylhydantoin (DBDMH) . Journal of the Chinese Chemical Society 63:2, pages 158-164.
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Suvendu Samanta, Shounak Ray, Abhisek Brata Ghosh & Papu Biswas. (2016) 3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) mediated metal-free mild oxidation of thiols to disulfides in aqueous medium. RSC Adv. 6:45, pages 39356-39363.
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Mohammad Abbasi & Arida Jabbari. (2015) One-pot conversion of alkyl halides to organic disulfides (disulfanes) using thiourea and hexamethyldisilazane (HMDS) in DMSO. Journal of the Iranian Chemical Society 13:1, pages 81-86.
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Zhanguo Chen, Yali Liu, Junli Hu & De’e Liu. (2015) Aminobromination of ethyl α-cyanocinnamate derivatives with 1,3-dibromo-5,5-dimethylhydantoin(DBDMH) as nitrogen and halogen sources. Chemical Research in Chinese Universities 31:1, pages 65-70.
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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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Ramanjaneyulu Rayala & Stanislaw F. Wnuk. (2012) Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1,3-dibromo-5,5-dimethylhydantoin. Tetrahedron Letters 53:26, pages 3333-3336.
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Giuseppe La Regina, Valerio Gatti, Valeria Famiglini, Francesco Piscitelli & Romano Silvestri. (2012) Venting-while-Heating Microwave-Assisted Synthesis of 3-Arylthioindoles. ACS Combinatorial Science 14:4, pages 258-262.
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ARASH GHORBANI-CHOGHAMARANI, MOHSEN NIKOORAZM, HAMID GOUDARZIAFSHAR, ALIREZA SHOKR & HOSEIN ALMASI. (2011) Metal-free oxidative coupling of thiols to disulfides using guanidinium nitrate or nitro urea in the presence of silica sulfuric acid. Journal of Chemical Sciences 123:4, pages 453-457.
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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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Vinod Kumar & Mahabir Parshad Kaushik. (2008) Efficient Oxidative Coupling of Thiols into Disulfides Using N - tert -Butyl- N -chlorocyanamide . Bulletin of the Chemical Society of Japan 81:1, pages 160-162.
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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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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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Ashraful Alam, Yutaka Takaguchi & Sadao Tsuboi. (2005) Simple, Extremely Fast, and High‐Yielding Oxidation of Thiols to Disulfides. ChemInform 36:41.
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