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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 181, 2006 - Issue 3
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Original Articles

Dinitrogen Tetroxide Impregnated Charcoal (N2O4/Charcoal): Selective Oxidation of Thiols to Disulfides or Thiosulfonates

Nasser Iranpoor Department of Chemistry, Shiraz University, Shiraz, Iran
,
Habib Firouzabadi Department of Chemistry, Shiraz University, Shiraz, Iran
&
Ali Reza Pourali Department of Chemistry, Shiraz University, Shiraz, Iran
Pages 473-479 | Received 17 Jan 2005, Accepted 04 Oct 2005, Published online: 01 Feb 2007

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Mohammad Soleiman-Beigi, Issa Yavari & Fatemeh Sadeghizadeh. (2018) A rapid, efficient and green procedure for transformation of alkyl halides/ tosylates to organochalcogens in water. Phosphorus, Sulfur, and Silicon and the Related Elements 193:1, pages 41-44.
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Ornella Ursini, Giancarlo Angelini & Franco Cataldo. (2017) Adsorption of dinitrogen tetroxide on activated carbon fabric derived from novolacs. Fullerenes, Nanotubes and Carbon Nanostructures 25:10, pages 589-601.
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Wenjie Liu, Cancan Wang, Yibo Huang, Qun Chen, Liang Wang & Mingyang He. (2016) Visible-light-mediated facile synthesis of disulfides using reusable TiO2/MoS2 nanocomposite photocatalyst. Synthetic Communications 46:15, pages 1268-1274.
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Thi Xuan Thi Luu, Thao-Tran Thi Nguyen, Thach Ngoc Le, Jens Spanget-Larsen & Fritz Duus. (2015) Fast and efficient green synthesis of thiosulfonate S-esters by microwave-supported permanganate oxidation of symmetrical disulfides. Journal of Sulfur Chemistry 36:3, pages 340-350.
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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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Articles from other publishers (30)

Calebe H. L. SilvaJéssica SoaresCarlos R. M. PeixotoJuliano B. AzeredoBruno S. de SouzaJuliano A. RohersMarcelo Godoi. (2023) Selective Synthesis of Symmetrical Thiosulfonates via Oxidative Coupling of Thiols Catalyzed by Diorganyl Diselenide. ChemistrySelect 8:41.
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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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Cheng-Li Yang, Xue-Jie Gao, Xin-Yi Jiang, Zhen Shi, Er-Jun Hao & Zhi-Bing Dong. (2022) Synthesis of Unsymmetric Thiosulfonates Starting from N-Substituted O -Thiocarbamates: Easy Access to the S–SO 2 Bond . The Journal of Organic Chemistry 87:17, pages 11656-11668.
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Yuan-Zhao Ji, Chi Zhang, Jun-Hu Wang, Hui-Jing Li & Yan-Chao Wu. (2021) Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions. Organic & Biomolecular Chemistry 19:42, pages 9291-9298.
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Xue Li, WeiBo Liao, Bin Huang, YuanYuan Zhang & JiangWei Wang. (2021) A metal-free approach for the synthesis of thiosulfonates from sulfonyl hydrazides. Journal of Chemical Research 45:11-12, pages 921-927.
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P. Mampuys, C. R. McElroyJ. H. ClarkR. V. A. Orru & B. U. W. Maes. (2019) Thiosulfonates as Emerging Reactants: Synthesis and Applications. Advanced Synthesis & Catalysis 362:1, pages 3-64.
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Mohammad Abbasi, Najmeh Nowrouzi & Saadat Mousavi. (2019) Aerobic Oxidation of Thiols and In Situ Generated Thiols to Symmetrical Disulfides (Disulfanes) Catalyzed by Na 2 S 4 O 6 . ChemistrySelect 4:42, pages 12227-12231.
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Dattatraya H. Dethe, Aparna Srivastava, Balu D. Dherange & B. Vijay Kumar. (2018) Unsymmetrical Disulfide Synthesis through Photoredox Catalysis. Advanced Synthesis & Catalysis 360:16, pages 3020-3025.
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Qian Chen, Yulin Huang, Xiaofeng Wang, Jiawei Wu & Guodian Yu. (2018) Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides. Organic & Biomolecular Chemistry 16:10, pages 1713-1719.
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Zhihong Peng, Xiao Zheng, Yingjun Zhang, Delie An & Wanrong Dong. (2018) H 2 O 2 -mediated metal-free protocol towards unsymmetrical thiosulfonates from sulfonyl hydrazides and disulfides in PEG-400 . Green Chemistry 20:8, pages 1760-1764.
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Xiaoji Li, Chao Zhou, Pinhui Diao, Yanqin Ge & Cheng Guo. (2017) Visible light induced decomposition of sulfonyl hydrazides using Pd/ZrO 2 nanocomposite photocatalyst. Tetrahedron Letters 58:13, pages 1296-1300.
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Arisson Tranquilino, Silvia R.C.P. Andrade, Ana Paula M. da Silva, Paulo H. Menezes & Roberta A. Oliveira. (2017) Non-expensive, open-flask and selective catalytic systems for the synthesis of sulfinate esters and thiosulfonates. Tetrahedron Letters 58:13, pages 1265-1268.
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Yong Zheng, Feng-Ling Qing, Yangen Huang & Xiu-Hua Xu. (2016) Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide. Advanced Synthesis & Catalysis 358:21, pages 3477-3481.
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Shan-Li Yi, Mei-Chao Li, Xin-Quan Hu, Wei-Min Mo & Zhen-Lu Shen. (2016) An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tert -butyl nitrite. Chinese Chemical Letters 27:9, pages 1505-1508.
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Palani Natarajan. (2015) Facile synthesis of symmetric thiosulfonates by oxidation of disulfide with oxone/MX (MX = KBr, KCl, NaBr and NaCl). Tetrahedron Letters 56:27, pages 4131-4134.
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Pieter Mampuys, Yanping Zhu, Tjøstil Vlaar, Eelco Ruijter, Romano V. A. Orru & Bert U. W. Maes. (2014) Sustainable Three-Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines. Angewandte Chemie International Edition 53:47, pages 12849-12854.
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Pieter Mampuys, Yanping Zhu, Tjøstil Vlaar, Eelco Ruijter, Romano V. A. Orru & Bert U. W. Maes. (2014) Sustainable Three‐Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines. Angewandte Chemie 126:47, pages 13063-13068.
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Masayuki Kirihara, Sayuri Naito, Yuki Nishimura, Yuki Ishizuka, Toshiaki Iwai, Haruka Takeuchi, Tomomi Ogata, Honoka Hanai, Yukari Kinoshita, Mari Kishida, Kento Yamazaki, Takuya Noguchi & Shiro Yamashoji. (2014) Oxidation of disulfides with electrophilic halogenating reagents: concise methods for preparation of thiosulfonates and sulfonyl halides. Tetrahedron 70:14, pages 2464-2471.
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A. Lattanzi. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 837 879 .
Satoshi Iwata, Masato Senoo, Takeshi Hata & Hirokazu Urabe. (2013) Synthesis of S -Aryl Arenethiosulfonates from N , N -Di(arenesulfonyl)hydrazines: Reduction of Sulfonyl Chlorides with an Organic Reagent . Heteroatom Chemistry 24:4, pages 336-344.
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Gaigai Liang, Jing Chen, Jiali Chen, Wanmei Li, Jiuxi Chen & Huayue Wu. (2012) Sc(OTf)3-catalyzed synthesis of thiosulfonates in ionic liquid-water. Tetrahedron Letters 53:50, pages 6768-6770.
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Gaigai Liang, Miaochang Liu, Jiuxi Chen, Jinchang Ding, Wenxia Gao & Huayue Wu. (2012) NBS‐Promoted Sulfenylation of Sulfinates with Disulfides Leading to Unsymmetrical or Symmetrical Thiosulfonates. Chinese Journal of Chemistry 30:7, pages 1611-1616.
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Gholamabbas Chehardoli, Mohammad Ali Zolfigol, Ezat Ghaemi, Elaheh Madrakian, Khodabakhsh Niknam & Shadpour Mallakpour. (2012) N 2 O 4 Chemisorbed onto n ‐Propylsilica Kryptofix 21 and Kriptofix 22 as Two New Functional Polymers for the Fast Oxidation of Urazoles and 1,4‐Dihydropyridines . Journal of Heterocyclic Chemistry 49:3, pages 596-599.
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Kiumars Bahrami, Mohammad M. Khodaei & Donya Khaledian. (2012) Synthesis of sulfonyl chlorides and thiosulfonates from H2O2–TiCl4. Tetrahedron Letters 53:3, pages 354-358.
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Masayuki Kirihara, Sayuri Naito, Yuki Ishizuka, Honoka Hanai & Takuya Noguchi. (2011) Oxidation of disulfides with Selectfluor™: concise syntheses of thiosulfonates and sulfonyl fluorides. Tetrahedron Letters 52:24, pages 3086-3089.
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Ali Reza Pourali & Fatemeh Fatemi. (2010) Selective nitration of phenols using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid under aprotic conditions. Chinese Chemical Letters 21:11, pages 1283-1286.
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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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Ming-Tiao Cai, Guang-Shu Lv, Jiu-Xi Chen, Wen-Xia Gao, Jin-Chang Ding & Hua-Yue Wu. (2010) CAN/I 2 -catalyzed Chemoselective Synthesis of Thiosulfonates by Oxidation of Disulfides or Thiols . Chemistry Letters 39:4, pages 368-369.
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José Luis García Ruano, Alejandro Parra & José Alemán. (2008) Efficient synthesis of disulfides by air oxidation of thiols under sonication. Green Chemistry 10:6, pages 706.
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Nasser Iranpoor, Habib Firouzabadi & Ali Reza Pourali. (2006) Dinitrogen Tetroxide Impregnated Charcoal (N 2 O 4 /Charcoal): Selective Oxidation of Thiols to Disulfides or Thiosulfonates. . ChemInform 37:24.
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