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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 6
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Original Articles

Nitric Acid Mediated Oxidative Transformation of Thiols to Disulfides

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Pages 1079-1085 | Received 25 Sep 2003, Published online: 21 Aug 2006

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (12)

Chiu Ling Ong, Thorsten Heidelberg, Joon Ching Juan & Nader Ghaffari Khaligh. (2021) Practical and efficient recyclable oxidative system for the preparation of symmetrical disulfides under aerobic conditions. Journal of Sulfur Chemistry 42:3, pages 281-294.
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Babak Mokhtari, Ali Reza Kiasat & Javid Monjezi. (2015) Imidazole Promoted Highly Efficient Large-Scale Thiol-Free Synthesis of Symmetrical Disulfides in Aqueous Media. Phosphorus, Sulfur, and Silicon and the Related Elements 190:10, pages 1573-1579.
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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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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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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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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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M. Saeed Abaee, MohammadM. Mojtahedi & Somayeh Navidipoor. (2010) Diethylamine-Catalyzed Dimerization of Thiols: An Inexpensive and Green Method for the Synthesis of Homodisulfides Under Aqueous Conditions. Synthetic Communications 41:2, pages 170-176.
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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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SudershanR. Gondi, DavidY. Son, EdwardR. Biehl & RajanK. Vempati. (2009) Easy and Rapid Method for Disulfide Syntheses Using Nanophase-Manganese (VII) Oxide Coated Clay. Phosphorus, Sulfur, and Silicon and the Related Elements 185:1, pages 34-39.
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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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Ali Reza Kiasat, Babak Mokhtari, Ali Savari & Foad Kazemi. (2007) Facile Solvent-Free Generation of Disulfide Dianion and its Use for Preparation of Symmetrical Disulfides. Phosphorus, Sulfur, and Silicon and the Related Elements 183:1, pages 178-182.
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Articles from other publishers (34)

Shiquan ShanSonghao PangYunwei Qu, Yongna LuXiamin ChengLin Li. (2023) Photooxidative Coupling of Thiols Promoted by Bromo(trichloro)methane in a Basic Aqueous Medium. Synlett 35:01, pages 113-117.
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Kyungmi Kim, Youngjin Shin & Junghyun Chae. (2023) Solvent-Selective Synthesis of Diaryl Disulfides and Arylthio Acetic Acids Using Thioglycolic Acid and Copper Catalysts. Synlett.
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Mohsen Khataminejad, Najmeh Nowrouzi, Dariush Saberi & Mahdi Aberi. (2023) Ultrasound‐assisted efficient aerobic oxidative coupling of thiols to disulfides with DiMIM‐CH 3 SO 4 as a recyclable ionic liquid catalyst in water: A green approach . ChemistrySelect 8:38.
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Mohammad Soleiman-Beigi, Zeinab Noroozian, Rokhsareh Sarai, Homa Kohzadi & Ali Naghipour. (2023) Palladium and zirconium nanoparticles immobilized on functionalized natural asphalt sulfonate as magnetically and recoverable nanocatalysts for the synthesis of symmetrical and unsymmetrical disulfides. Reaction Kinetics, Mechanisms and Catalysis.
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Lijun Xue, Hangke Ma, Weijie Liu, Nicolas DucheminFanming Zeng, Jie Zhang, Huanqing Zhang, Kexin Yang & Yun Jin Hu. (2023) Constructive on-DNA Thiol Aerial Oxidization for DNA-Encoded Library Synthesis. ACS Omega 8:26, pages 24072-24077.
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Zhiguang Zhang, Xiaojie Lan, Xiaomin Zhang, Yanmei Liu, Jinxin Gao, Bingzhu Zhang & Haixia Wu. (2023) ABNO‐Catalyzed Aerobic Oxidation of Thiols to Disulfides under Atmospheric Pressure. Asian Journal of Organic Chemistry 12:3.
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Chaojie Zhu, Dongfang Wu, Huili Liu, Congwei Meng & Tiandi Tang. (2022) Transformation of thiols to disulfides via an oxidant-free radical pathway on the zeolite ETS-10 . Green Chemistry 24:23, pages 9033-9039.
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Xiaoman Li, Jiali Fan, Dezhi Cui, Hui Yan, Shiquan Shan, Yongna Lu, Xiamin Cheng & Teck‐Peng Loh. (2022) Catalyst‐ and Metal‐Free Photo‐Oxidative Coupling of Thiols with BrCCl 3 . European Journal of Organic Chemistry 2022:23.
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Chiu Ling Ong, Thorsten Heidelberg, Joon Ching Juan & Nader Ghaffari Khaligh. (2022) Metal-free and green synthesis of a series of new bis(2-alkylsulfanyl-[1,3,4]thiadiazolyl)-5,5′-disulfides and 2,2′-Dibenzothiazyl disulfide via oxidative self-coupling using hydrogen peroxide. Polyhedron 213, pages 115610.
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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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Monalisa Kundu & Anup Kumar Misra. (2021) Direct Synthesis of Unsymmetrical Glycosyl Disulfides from Glycosyl Bromides. European Journal of Organic Chemistry 2021:26, pages 3759-3767.
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Silvia Anselmi, Siyu Liu, Seong-Heun Kim, Sarah M. Barry, Thomas S. Moody & Daniele Castagnolo. (2021) A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent. Organic & Biomolecular Chemistry 19:1, pages 156-161.
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Austin Curnutt, Kaylee Smith, Emily Darrow & Keisha B. Walters. (2020) Chemical and Microstructural Characterization of pH and [Ca2+] Dependent Sol-Gel Transitions in Mucin Biopolymer. Scientific Reports 10:1.
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Rongjun He, Jia Pan, John P. Mayer & Fa Liu. (2020) The Chemical Methods of Disulfide Bond Formation and Their Applications to Drug Conjugates. Current Organic Chemistry 23:25, pages 2802-2821.
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Emeline Benoit, Ahmed Fnaiche & Alexandre Gagnon. (2019) Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid. Beilstein Journal of Organic Chemistry 15, pages 1162-1171.
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Ishani Bhaumik, Kunal Pal, Utsab Debnath, Parimal Karmakar, Kuladip Jana & Anup Kumar Misra. (2019) Natural product inspired allicin analogs as novel anti-cancer agents. Bioorganic Chemistry 86, pages 259-272.
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Benchikh Imen, Djafri Fatiha, Djafri Ayada, Tabti Affaf & Franck Launay. (2017) Synthesis and characterization of Cr-ZSM-5 composite in fluoride medium and its performance in oxidation reaction of 2-mercaptobenzotiazole. International Journal of Clothing Science and Technology 29:4, pages 483-490.
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S.L. Zhao, F.S. Chen, J. Zhang, S.B. Ren, H.D. Liang & S.S. Li. (2015) On-line flame AAS determination of traces Cd(II) and Pb(II) in water samples using thiol-functionalized SBA-15 as solid phase extractant. Journal of Industrial and Engineering Chemistry 27, pages 362-367.
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Yongsheng Zhou. (2015) Deep Eutectic Mixture Catalysed the Synthesis of Disulfides Using Bunte Salts as Thiol Surrogates. Journal of Chemical Research 39:6, pages 332-335.
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Saima, Aditya G. Lavekar, Rajesh Kumar & Arun K. Sinha. (2015) Bovine serum albumin triggered waste-free aerobic oxidative coupling of thiols into disulphides on water: An extended synthesis of bioactive dithiobis(phenylene)bis(benzylideneimine) via sequential oxidative coupling–condensation reactions in one pot from aminothiophenol and benzaldehyde. Journal of Molecular Catalysis B: Enzymatic 116, pages 113-123.
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Mohsen Nikoorazm, Arash Ghorbani-Choghamarani, Farshid Ghorbani, Houri Mahdavi & Zahra Karamshahi. (2014) Bidentate salen Cu(II) complex functionalized on mesoporous MCM-41 as novel nano catalyst for the oxidative coupling of thiols into disulfides using urea hydrogen peroxide (UHP). Journal of Porous Materials 22:1, pages 261-267.
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Ning Chen, Xin Zhong, Pingfan Li & Jiaxi Xu. (2015) A Mild Radical Method for the Dimerzation of Dithiocarbamates. European Journal of Organic Chemistry 2015:4, pages 802-809.
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Holisoa Rajerison, François Guérard, Marie Mougin-Degraef, Mickael Bourgeois, Isidro Da Silva, Michel Chérel, Jacques Barbet, Alain Faivre-Chauvet & Jean-François Gestin. (2014) Radioiodinated and astatinated NHC rhodium complexes: Synthesis. Nuclear Medicine and Biology 41, pages e23-e29.
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Bablee Mandal & Basudeb Basu. (2014) Recent advances in S–S bond formation. RSC Advances 4:27, pages 13854.
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Heba T. Abdel-Mohsen, Kavitha Sudheendran, Jürgen Conrad & Uwe Beifuss. (2013) Synthesis of disulfides by laccase-catalyzed oxidative coupling of heterocyclic thiols. Green Chemistry 15:6, pages 1490.
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Ben Dong, Shuai Lu, Jun Jiang, Wenjing Zhang, Weimin Zhu, Mingsheng Tang & Guanyu Yang. (2012) Aerobic oxidative radical coupling catalyzed by TEMPO for the preparation of 2,2′-dibenzothiazole disulfide. Journal of Chemical Technology & Biotechnology 87:3, pages 341-345.
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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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Mahmood Tajbakhsh, Moslem M. Lakouraj & Majid S. Mahalli. (2008) The rapid and efficient synthesis of disulfides from alkyl and acyl halides. Monatshefte für Chemie - Chemical Monthly 139:12, pages 1453-1456.
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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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Scott C. Banfield, Alvaro Takeo Omori, Hannes Leisch & Tomas Hudlicky. (2007) Unexpected Reactivity of the Burgess Reagent with Thiols:  Synthesis of Symmetrical Disulfides. The Journal of Organic Chemistry 72:13, pages 4989-4992.
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Morteza Montazerozohori, Shiva Joohari, Bahador Karami & Nasrin Haghighat. (2007) Fast and Highly Efficient Solid State Oxidation of Thiols. Molecules 12:3, pages 694-702.
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Recep Ozen & Fatma Aydin. (2006) Oxidation of Thiols to Disulfides with Molecular Oxygen in Subcritical Water. Monatshefte für Chemie - Chemical Monthly 137:3, pages 307-310.
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Fatma Aydin & Recep Ozen. (2019) 3-Carboxypyridinium Trichloroacetatochromate (CPTCAC): As a Mild and Effective New Reagent for the Thiols to Disulfides. Journal of Chemical Research 2005:4, pages 224-226.
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Anup Kumar Misra & Geetanjali Agnihotri. (2004) Nitric Acid Mediated Oxidative Transformation of Thiols to Disulfides.. ChemInform 35:32.
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