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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 1
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Original Articles

Preparation of Disulfides by the Oxidation of Thiols Using Bromine

Xiaoming Wu Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska, 68588–0304
,
Reuben D. Rieke Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska, 68588–0304
&
Lishan Zhu Rieke Metals, Inc., 6133 Heide Lane, Lincoln, Nebraska, 68502
Pages 191-196 | Received 15 May 1995, Published online: 21 Aug 2006

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Ngan-Giang Thi Nguyen, Xuan-Triet Nguyen, Ngoc-Huy Nguyen, Thi Xuan Thi Luu & Xuan-Tien Dao. (2022) Ground solid permanganate oxidative coupling of thiols into symmetrical/unsymmetrical disulfides: selective and improved process. Journal of Sulfur Chemistry 43:6, pages 593-605.
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Askar Sabet, Eskandar Kolvari, Nadiya koukabi, Abdolrasool Fakhraee, Motahareh Ramezanpour & Gholamreza Bahmannia. (2015) Oxidative coupling of aromatic thiols to corresponding disulfides using magnetic particle-supported sulfonic acid catalyst and hydrogen peroxide under mild conditions. Journal of Sulfur Chemistry 36:3, pages 300-307.
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Ying He, Dongliang Hang & Ming Lu. (2012) A Simple and Practical Method for the Oxidation of Thiols to Disulfides at Mild Conditions Without Solvents. Phosphorus, Sulfur, and Silicon and the Related Elements 187:9, pages 1118-1124.
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Morteza Montazerozohori & Leila Zamani Fradombe. (2010) Aerobic Oxidation of Some Arylthiols Catalyzed by a New Manganese (III) Schiff-Base Complex. Phosphorus, Sulfur, and Silicon and the Related Elements 185:3, pages 509-515.
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Xin Wang, Xianliang Chen, Xiaojing Wu, Jingqiu Tao & Ling Cheng. (2009) Green Route for Rapid Synthesis of 2,2′-Dithiobis(benzothiazole) by Microwave Irradiation. Synthetic Communications 39:19, pages 3453-3458.
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Wei-Li Dong, Guang-Ying Huang, Zheng-Ming Li & Wei-Guang Zhao. (2009) A Convenient Method for the Aerobic Oxidation of Thiols to Disulfides. Phosphorus, Sulfur, and Silicon and the Related Elements 184:8, pages 2058-2065.
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MoslemM. Lakouraj & Keivan Ghodrati. (2008) Carboxy Pyridinium Bromide Perbromide Reagents, Part I: Selective Oxidation of Thiols and Sulfides. Phosphorus, Sulfur, and Silicon and the Related Elements 183:6, pages 1432-1439.
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Firdous Imran Ali, Imran Ali Hashmi, Bina S. Siddiqui & Munawwer Rasheed. (2007) Simple Method for the Preparation of Symmetrical Alkyl and Aryl Disulfides with Alkyl Sulfonyl Halides in Nitrogenous Base. Synthetic Communications 37:15, pages 2461-2465.
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Majid M. Heravi, Fatemeh Derikvand, Hossein A. Oskooie, Rahim Hekmat Shoar & Mahmood Tajbakhsh. (2007) Silica‐Supported bis (Trimethylsilyl) Chromate: Oxidation of Thiols to Their Corresponding Disulfides. Synthetic Communications 37:3, pages 513-517.
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MohammedM. Hashemi, Hossein Ghafuri & Zahed Karimi-Jaberi. (2006) N-Chlorosuccinimide: A simple and efficient reagent for the preparation of symmetrical disulfides. Journal of Sulfur Chemistry 27:2, pages 165-167.
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Nasser Iranpoor, Habib Firouzabadi & Ali Reza Pourali. (2006) Dinitrogen Tetroxide Impregnated Charcoal (N2O4/Charcoal): Selective Oxidation of Thiols to Disulfides or Thiosulfonates. Phosphorus, Sulfur, and Silicon and the Related Elements 181:3, pages 473-479.
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Ashraful Alam, Yutaka Takaguchi & Sadao Tsuboi. (2005) Simple, Extremely Fast, and High‐Yielding Oxidation of Thiols to Disulfides. Synthetic Communications 35:10, pages 1329-1333.
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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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Anup Kumar Misra & Geetanjali Agnihotri. (2004) Nitric Acid Mediated Oxidative Transformation of Thiols to Disulfides. Synthetic Communications 34:6, pages 1079-1085.
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Issa Yavari, Mina Haghdadi & Rahebeh Amiri. (2004) AB INITIO MOLECULAR ORBITAL STUDY OF 1,2-DITHIANE AND 1,2,4,5-TETRATHIANE. Phosphorus, Sulfur, and Silicon and the Related Elements 179:10, pages 2015-2023.
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Mohammad Mehdi Khodaei, Peyman Salehi, Maryam Goodarzi & Ateesa Yazdanipour. (2004) γ‐PCC and γ‐PCC‐SiO2 as Efficient Reagents for Oxidation of Thiols to Disulfides. Synthetic Communications 34:20, pages 3661-3666.
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Ping Zhong & Meng-Ping Guo. (2001) PREPARATION OF DISULFIDES BY THE OXIDATION OF THIOLS USING TRICHLOROISOCYANURIC ACID. Synthetic Communications 31:12, pages 1825-1828.
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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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Masao Hirano, Shigetaka Yakabe, Nobuteru Uraoka & Takashi Morimoto. (1998) SYNTHESIS OF DISULFIDES BY THE OXIDATIVE COUPLING OF THIOLS WITH CALCIUM HYPOCHLORITE AND SILICA GEL IN HEXANE. Organic Preparations and Procedures International 30:3, pages 360-363.
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Masao Hirano, Shigetaka Yakabe, Masataka Fukami & Takashi Morimoto. (1997) An Environmentally Friendly Oxidation of Thiols to Disulfides by Calcium Hypochlorite and Montmorillonite K10 in Hexane. Synthetic Communications 27:16, pages 2783-2788.
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Paolo Donati, Tania Pomili, Luca Boselli & Pier P. Pompa. (2020) Colorimetric Nanoplasmonics to Spot Hyperglycemia From Saliva. Frontiers in Bioengineering and Biotechnology 8.
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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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Rahmatollah Rahimi, Shabnam Pordel & Mahboubeh Rabbani. (2016) Synthesis of Bi2WO6 nanoplates using oleic acid as a green capping agent and its application for thiols oxidation. Journal of Nanostructure in Chemistry 6:2, pages 191-196.
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Elise M. Hall, Kristina Tschulik, Christopher Batchelor-McAuley & Richard G. Compton. (2016) Electrochemical bromination of organosulfur containing species for the determination of the strength of garlic (A. sativum). Food Chemistry 199, pages 817-821.
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Avelino Corma, Tania Ródenas & Maria J. Sabater. (2012) Aerobic oxidation of thiols to disulfides by heterogeneous goldcatalysts. Chem. Sci. 3:2, pages 398-404.
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Abdollah ShojaeiFallahFallah, Mohamad RezvaniAliAli & Majid Heravi. (2011) H5PV2Mo10O40 as an efficient catalyst for the oxidation of thiols to the corresponding disulfides using hydrogen peroxide as the oxidant. Journal of the Serbian Chemical Society 76:7, pages 955-963.
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Hyung Jun Kim, Jun Hee Yoon & Sangwoon Yoon. (2010) Photooxidative Coupling of Thiophenol Derivatives to Disulfides. The Journal of Physical Chemistry A 114:45, pages 12010-12015.
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Devender Singh, Fábio Z. Galetto, Letiére C. Soares, Oscar E. Dorneles Rodrigues & Antonio Luiz Braga. (2010) Metal‐Free Air Oxidation of Thiols in Recyclable Ionic Liquid: A Simple and Efficient Method for the Synthesis of Disulfides. European Journal of Organic Chemistry 2010:14, pages 2661-2665.
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Ahmad Shaabani, Naser Safari, Samad Shoghpour & Ali Hossein Rezayan. (2008) Silica-supported cobalt(II) tetrasulfophthalocyanine catalyzed aerobic oxidation of thiols to disulfides under neutral conditions. Monatshefte für Chemie - Chemical Monthly 139:6, pages 613-615.
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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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Syed Tasadaque A. Shah, Khalid M. Khan, Miriam Fecker & Wolfgang Voelter. (2003) A novel method for the syntheses of symmetrical disulfides using CsF–Celite as a solid base. Tetrahedron Letters 44:35, pages 6789-6791.
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Christopher J. Burns, Leslie D. Field, Jacqueline Morgan, Damon D. Ridley & Valentina Vignevich. (1999) Preparation of cyclic disulfides from bisthiocyanates. Tetrahedron Letters 40:35, pages 6489-6492.
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X. WU, R. D. RIEKE & L. ZHU. (2010) ChemInform Abstract: Preparation of Disulfides by the Oxidation of Thiols Using Bromine.. ChemInform 27:23.
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