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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 7
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Original Articles

Solid State Oxidation of Thiols to Disulfides Using Ammonium Persulfate

Rajender S. Varma Department of Chemistry and Texas Research Institute for Environmental Studies (TRIES), Sam Houston State University, Huntsville, Texas, 77341-2117, U.S.A.; Houston Advanced Research Center (HARC), 4800 Research Forest Drive, The Woodlands, Texas, 77381, U.S.A.
,
Harshadas M. Meshram Houston Advanced Research Center (HARC), 4800 Research Forest Drive, The Woodlands, Texas, 77381, U.S.A.; Organic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
&
Rajender Dahiya Department of Chemistry and Texas Research Institute for Environmental Studies (TRIES), Sam Houston State University, Huntsville, Texas, 77341-2117, U.S.A.; M.L.N. College, Yamuna Nagar, 135001, Haryana, India
Pages 1249-1255 | Received 09 Aug 1999, Published online: 04 Dec 2007

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AmerM. Alanazi, EbtehalS. Al-Abdullah, NasserR. El-Brollosy & AliA. El-Emam. (2014) Unusual Sulfuric Acid-Induced Thiol Oxidation on Dehydrative Cyclization of Potassium N′-(1-Adamantylcarbonyl)Dithiocarbazate at Room Temperature. Phosphorus, Sulfur, and Silicon and the Related Elements 189:4, pages 477-482.
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Madhudeepa Dey, Siddhartha Sankar Dhar & Mukul Kalita. (2013) Novel Method of Synthesis of Quaternary Ammonium Tribromides and Investigation of Catalytic Role of Benzyltrimethylammonium Tribromide in Oxidation of Alcohols to Carbonyl Compounds. Synthetic Communications 43:12, pages 1734-1742.
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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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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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Hossein Ghafuri & Mohammed M. Hashemi. (2009) A simple, economical, and catalyst-free oxidation of thiols to disulfides. Journal of Sulfur Chemistry 30:6, pages 578-580.
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Huilong Xiao, Jiuxi Chen, Miaochang Liu, Huayue Wu & Jinchang Ding. (2009) An Approach to Disulfide Synthesis Promoted by Sulfonyl Chloride in Sodium Bicarbonate Aqueous Media. Phosphorus, Sulfur, and Silicon and the Related Elements 184:10, pages 2553-2559.
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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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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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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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Peyman Salehi, Mohammad Ali Zolfigol & Leila Bazaz Tolami. (2004) EFFICIENT AND SELECTIVE OXIDATION OF THIOLS TO DISULFIDES BY 1,4-DIAZABICYCLO[2.2.2]OCTANE-DI-N-OXIDE-DI-PERHYDRATE UNDER NEUTRAL AND HETEROGENEOUS CONDITIONS. Phosphorus, Sulfur, and Silicon and the Related Elements 179:9, pages 1777-1781.
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A. R. Hajipour, S. E. Mallakpour & H. Adibi. (2002) A Selective Solid State Oxidation of Sulfides and Thiols with Benzyltriphenylphosphonium Peroxymonosulfate. Phosphorus, Sulfur, and Silicon and the Related Elements 177:10, pages 2277-2284.
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Arnab Chowdhury, Vinod Gour, Basab Kanti Das, Saurav Chatterjee & Anupam Bandyopadhyay. (2023) Rapid and Highly Productive Assembly of a Disulfide Bond in Solid-Phase Peptide Macrocyclization. Organic Letters 25:8, pages 1280-1284.
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Ebrahim Kianmehr, Fatemeh Doraghi & Alireza Foroumadi. (2022) Nickel-Catalyzed Regioselective Thiolation of Anilides with Thiols. Synthesis 54:10, pages 2464-2472.
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K. V. Shabalin, L. I. Musin, L. E. Foss, O. A. Nagornova, V. I. Morozov, D. N. Borisov & M. R. Yakubov. (2022) Preparation of Redox Ion-Exchange Materials Based on Petroleum Asphaltenes. Petroleum Chemistry 62:2, pages 222-228.
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Nasrin Masnabadi, Mohammad Hadi Ghasemi, Mostafa Hossein Beyki & Mohammad Sadeghinia. (2016) Oxidative dimerization of thiols to disulfide using recyclable magnetic nanoparticles. Research on Chemical Intermediates 43:3, pages 1609-1618.
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Ana M. Toma, Ciprian I. Raţ, Octavian D. Pavel, Christopher Hardacre, Tobias Rüffer, Heinrich Lang, Michael Mehring, Anca Silvestru & Vasile I. Pârvulescu. (2017) Heterocyclic bismuth( iii ) compounds with transannular N→Bi interactions as catalysts for the oxidation of thiophenol to diphenyldisulfide . Catalysis Science & Technology 7:22, pages 5343-5353.
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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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A. Lattanzi. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 837 879 .
Roya Esmaili & Davood Nematollahi. (2013) Electrochemical Method for the Synthesis of Disulfides of 2-(Benzo[ d ]thiazol(or oxazol)-2-ylamino)-5-morpholinobenzenethiol . The Journal of Organic Chemistry 78:10, pages 5018-5021.
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Edward J. Behrman & Sharon R. Neufeldt. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
H.M. Meshram, N. Nageswara Rao, L. Chandrasekhara Rao & N. Satish Kumar. (2012) Microwave assisted catalyst-free synthesis of azaarene-substituted 3-hydroxy-2-oxindoles by the functionalization of sp3 C–H bond in methyl pyridine. Tetrahedron Letters 53:31, pages 3963-3966.
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Mohammad Kazem Mohammadi, Shahriare Ghammamy & Mohammad Hossein Farjam. (2011) Microwave Assisted, Synthesis of Symmetrical Disulfides with Triethylammonium Halochromates, (C2H5)3NH+[CrO3X]-(X=F, Cl). International Journal of Chemical Engineering and Applications, pages 221-224.
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Ashish Kumar Singh & M.A. Quraishi. (2009) Effect of 2,2′ benzothiazolyl disulfide on the corrosion of mild steel in acid media. Corrosion Science 51:11, pages 2752-2760.
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Ishtiaque Ahamad & M.A. Quraishi. (2009) Bis (benzimidazol-2-yl) disulphide: An efficient water soluble inhibitor for corrosion of mild steel in acid media. Corrosion Science 51:9, pages 2006-2013.
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Ramin Ghorbani‐Vaghei, Mohammad Ali Zolfigol, Nasrin Moshfeghifar, Nadiya Koukabi & Gholamabbas Chehardoli. (2013) Poly( N ‐Bromobenzene‐1,3‐Disulfonylamide), N,N,N′,N′ ‐Tetrabromobenzene‐1,3‐Disulfonylamide and DABCO‐Bromine Complex: As Novel Reagents for the Oxidative Coupling of Thiols to Disulfides . Journal of the Chinese Chemical Society 54:3, pages 791-794.
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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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I. V. Koval’. (2007) Reactions of thiols. Russian Journal of Organic Chemistry 43:3, pages 319-346.
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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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Esmail Tammari, Naser Mirazi & Davood Nematollahi. (2006) Synthesis of catecholthioethers by the selective oxidation of catechols in competition with 2-mercaptobenzoxazole. Mendeleev Communications 16:5, pages 285-286.
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Davood Nematollahi & Esmail Tammari. (2005) Electroorganic Synthesis of Catecholthioethers. The Journal of Organic Chemistry 70:19, pages 7769-7772.
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Ardeshir Khazaei, Abbas Amini Manesh & Amin Rostami. (2019) N-Bromophthalimide [NBPI] as a Powerful Oxidizing Agent for the Facile and Chemoselective Oxidation of Thiols to Symmetrical Disulfides. Journal of Chemical Research 2005:6, pages 391-393.
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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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Mohammed M. Hashemi, Zahed Karimi-Jaberi & Bagher Eftekhari-Sis. (2019) Solid State Oxidation of Phenols to Quinones with Ammonium Persulfate/Wet SiO 2 . Journal of Chemical Research 2005:3, pages 160-161.
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Mahmood Tajbakhsh, Rahman Hosseinzadeh & Alireza Shakoori. (2004) 2,6-Dicarboxypyridinium chlorochromate: an efficient and selective reagent for the oxidation of thiols to disulfides and sulfides to sulfoxides. Tetrahedron Letters 45:9, pages 1889-1893.
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Rajender S. Varma. (2002) Clay and clay-supported reagents in organic synthesis. Tetrahedron 58:7, pages 1235-1255.
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Rajender S. Varma, Harshadas M. Meshram & Rajender Dahiya. (2010) ChemInform Abstract: Solid State Oxidation of Thiols to Disulfides Using Ammonium Persulfate.. ChemInform 31:33.
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