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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 3
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Original Articles

A Facile Synthesis of Unsymmetrical Thiolsulfonates via Sulfonylation of Mercaptans1

M. G. Ranasinghe Department of Chemistry, Purdue University, West Lafayette, IN, 47907
&
P. L. Fuchs Department of Chemistry, Purdue University, West Lafayette, IN, 47907
Pages 227-230 | Published online: 05 Dec 2006

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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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Sechoing Lin, Brian Moon, KennethT. Porter, CraigA. Rossman, Thomas Zennie & James Wemple. (2000) A CONTINUOUS PROCEDURE FOR PREPARATION OF para FUNCTION ALIZED AROMATIC THIOLS USING NEWMAN-KWART CHEMISTRY. Organic Preparations and Procedures International 32:6, pages 547-555.
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Articles from other publishers (28)

Ashvani Yadav, Rohit Kumar & Virendra Prasad. (2024) Hypervalent Iodine Mediated Synthesis of Thiosulfonates from Sulfonyl Hydrazides and Their Transformation into Symmetrical Disulfides. Synthesis.
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Martin Frandsen, Kassem El‐Chami, Johan Palmfeldt, Jakob Melgaard Smidt, Maja E. T. Langballe, Alexander Sandahl & Kurt V. Gothelf. (2023) Automated Solid‐Phase Oligo(disulfide) Synthesis. Angewandte Chemie International Edition 62:23.
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Martin Frandsen, Kassem El‐Chami, Johan Palmfeldt, Jakob Melgaard Smidt, Maja E. T. Langballe, Alexander Sandahl & Kurt V. Gothelf. (2023) Automated Solid‐Phase Oligo(disulfide) Synthesis. Angewandte Chemie 135:23.
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Xuezhen Li, Ping Liu, Jing He, Weiwei Li, Zhen Yang, Yueting Wei, Yu Wei & Yanlong Gu. (2021) TBAI-catalyzed ring-opening sulfonylations of benzothiazoles and arylsulfonyl hydrazides. Green Synthesis and Catalysis 2:4, pages 381-384.
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Cheng-Mi Huang, Jian Li, Shun-Yi Wang & Shun-Jun Ji. (2020) TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols: Construction of thiosulfonate under transition-metal free conditions. Chinese Chemical Letters 31:7, pages 1923-1926.
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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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Xinxing Gong, Xiaofang Li, Wenlin Xie, Jie Wu & Shengqing Ye. (2019) An unexpected reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and thiourea under photoinduced conditions. Organic Chemistry Frontiers 6:11, pages 1863-1867.
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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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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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Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts & James E. Thomson. (2012) The conjugate addition of enantiomerically pure lithium amides as chiral ammonia equivalents part II: 2005−2011. Tetrahedron: Asymmetry 23:15-16, pages 1111-1153.
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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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Ahmad El-Awa, Mohammad N. Noshi, Xavier Mollat du Jourdin & Philip L. Fuchs. (2009) Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety. Chemical Reviews 109:6, pages 2315-2349.
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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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Jos? I. Candela-Lena, Stephen G. Davies, Paul M. Roberts, Bruno Roux, Angela J. Russell, Elena M. S?nchez-Fern?ndez & Andrew D. Smith. (2006) Asymmetric synthesis of ?-mercapto-?-amino acid derivatives: application to the synthesis of polysubstituted thiomorpholines. Tetrahedron: Asymmetry 17:7, pages 1135-1145.
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Marie-Lyne Alcaraz, Stéphanie Atkinson, Philip Cornwall, Alison C. Foster, Duncan M. Gill, Lesley A. Humphries, Philip S. Keegan, Richard Kemp, Eric Merifield, Robert A. Nixon, Allison J. Noble, Darren O'Beirne, Zakariya M. Patel, Jacob Perkins, Paul Rowan, Paul Sadler, John T. Singleton, James Tornos, Andrew J. Watts & Ian A. Woodland. (2005) Efficient Syntheses of AZD4407 via Thioether Formation by Nucleophilic Attack of Organometallic Species on Sulphur. Organic Process Research & Development 9:5, pages 555-569.
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Adrian L. Schwan. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Raechelle A. D'SaYuhong WangPatrick H. RuaneBrett M. ShowalterJoseph E. SaavedraKeith M. DaviesMichael L. CitroMelissa N. BoothLarry K. KeeferJohn P. Toscano. (2002) Preparation and Reactivity of O 2 -Sulfonated Diazeniumdiolates . The Journal of Organic Chemistry 68:2, pages 656-657.
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J.V.N. Vara Prasad, A. Panapoulous & John R. Rubin. (2000) Thiocyanation of alkylanilines. A simple and efficient synthesis of thiosulfonates containing 2-aminobenzothiazole. Tetrahedron Letters 41:21, pages 4065-4068.
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J. V. N. Vara Prasad. (2000) Synthesis of Heterocyclic Thiosulfonates. Organic Letters 2:8, pages 1069-1072.
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Hiroyuki Takeda, Satoru Shimada, Satomi Ohnishi, Fusae Nakanishi & Hiro Matsuda. (1998) Preparation of 1-alkynyl 2-(trimethylsilyl)ethyl sulfides as thiolate anion precursors for self-assembled monolayers. Tetrahedron Letters 39:22, pages 3701-3704.
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Bradley D. Tait, Susan Hagen, John Domagala, Edmund L. Ellsworth, Christopher Gajda, Harriet W. Hamilton, J. V. N. Vara Prasad, Donna Ferguson, Neil Graham, Donald Hupe, Carolyn Nouhan, Peter J. Tummino, Christine Humblet, Elizabeth A. Lunney, Alexander Pavlovsky, John Rubin, Stephen J. Gracheck, Eric T. Baldwin, T. N. Bhat, John W. Erickson, Sergei V. Gulnik & Beishan Liu. (1997) 4-Hydroxy-5,6-dihydropyrones. 2. Potent Non-Peptide Inhibitors of HIV Protease. Journal of Medicinal Chemistry 40:23, pages 3781-3792.
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Susan E. Hagen, J. V. N. Vara Prasad, Frederick E. Boyer, John M. Domagala, Edmund L. Ellsworth, Christopher Gajda, Harriet W. Hamilton, Larry J. Markoski, Bruce A. Steinbaugh, Bradley D. Tait, Elizabeth A. Lunney, Peter J. Tummino, Donna Ferguson, Donald Hupe, Carolyn Nouhan, Stephen J. Gracheck, James M. Saunders & Steven VanderRoest. (1997) Synthesis of 5,6-Dihydro-4-hydroxy-2- pyrones as HIV-1 Protease Inhibitors:  The Profound Effect of Polarity on Antiviral Activity. Journal of Medicinal Chemistry 40:23, pages 3707-3711.
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J. V. N. Vara Prasad. (2009) Synthesis of 2‐aryl‐4‐hydroxy‐5‐thio substituted 1,3‐thiazin‐6‐ones via sulfenylation of 2‐aryl‐4‐hydroxy‐[1,3]thiazin‐6‐ones with sulfenyl chlorides . Journal of Heterocyclic Chemistry 33:6, pages 1599-1603.
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Seong Heon Kim, Zhendong Jin & P.L Fuchs. (1995) Synthesis of beta-substituted cyclopentenones via carbon alkylation of metalated gamma-methoxycyclopentenyl phenylsulfonyl anion. Tetrahedron Letters 36:26, pages 4537-4538.
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. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1103 1295 .
Philip C. Bulman Page, Robin D. Wilkes & Dominic Reynolds. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 113 275 .
Young Jun Park, Hyun Ho Shin & Yong Hae Kim. (1992) Convenient One-Pot Synthesis of Sulfonyl Chlorides from Thiols Using Sulfuryl Chloride and Metal Nitrate. Chemistry Letters 21:8, pages 1483-1486.
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M. G. RANASINGHE & P. L. FUCHS. (2016) ChemInform Abstract: A Facile Synthesis of Unsymmetrical Thiolsulfonates via Sulfonylation of Mercaptans.. ChemInform 19:36.
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