1146-42-5Relevant academic research and scientific papers
Synthesis of Symmetrical and Unsymmetrical Thiosulfonates from Disulfides through Electrochemically Induced Disulfide Bond Metathesis and Site-Selective Oxidation
Strehl, Julia,Hilt, Gerhard
supporting information, (2021/10/14)
The anodic generation of symmetrical and unsymmetrical thiosulfonates is presented. First, the oxidation of disulfides yielding symmetrical thiosulfonates was realized. The direct synthesis is performed using a simple quasi-divided cell design, whereby using a supporting electrolyte is unnecessary. Its principle was then expanded to the conversion of unsymmetrical disulfides that were generated in situ through metathesis of two symmetrical disulfides. This enables a direct access to unsymmetrical thiosulfonates without any pre-functionalization or elaborate synthesis of the starting materials for the first time. The reaction scope was investigated by converting differently functionalized aliphatic and aromatic disulfides in moderate to very good yields. Furthermore, a sensitivity assessment for an improved reproducibility and a robustness screen to determine the compatibility of the reaction against functional groups were performed.
Visible-light mediated sulfonylation of thiols via insertion of sulfur dioxide
Nair, Akshay M.,Kumar, Shreemoyee,Halder, Indranil,Volla, Chandra M. R.
supporting information, p. 5897 - 5901 (2019/06/24)
A simple and efficient visible-light mediated synthesis of thiosulfonates via a radical-radical coupling of sulfenyl radicals and arylsulfonyl radicals was developed. The reaction of thiols, aryldiazonium tetrafluoroborates and DABSO proceeded at room temperature using 5 mol% eosin Y. The reaction displayed wide functional group tolerance and delivered the unsymmetrical thiosulfonates in good to excellent yields.
Ammonium iodide-mediated electrosynthesis of unsymmetrical thiosulfonates from arenesulfonohydrazides and thiols
Terent'ev, Alexander O.,Mulina, Olga M.,Ilovaisky, Alexey I.,Kokorekin, Vladimir A.,Nikishin, Gennady I.
, p. 80 - 82 (2019/02/20)
Unsymmetrical thiosulfonates were synthesized from thiols and arenesulfonohydrazides by their electrolysis in undivided cell equipped with graphite anode and stainless steel cathode under high current density applying NH4I both as a redox catal
H2O2-mediated metal-free protocol towards unsymmetrical thiosulfonates from sulfonyl hydrazides and disulfides in PEG-400
Peng, Zhihong,Zheng, Xiao,Zhang, Yingjun,An, Delie,Dong, Wanrong
supporting information, p. 1760 - 1764 (2018/04/30)
A green and practical protocol between sulfonyl hydrazides and disulfides is herein reported for the synthesis of unsymmetrical thiosulfonates with the assistance of H2O2 in PEG-400, releasing N2 and H2O as the byproducts. The efficient and compatible process was considered to take place in the absence of metallic catalysts through a radical mechanism as determined by EPR analysis.
Copper-Catalyzed TBHP-Mediated Radical Cross-Coupling Reaction of Sulfonylhydrazides with Thiols Leading to Thiosulfonates
Zhang, Guo-Yu,Lv, Shuai-Shuai,Shoberu, Adedamola,Zou, Jian-Ping
, p. 9801 - 9807 (2017/09/22)
A tert-butyl hydroperoxide (TBHP)-mediated coupling of sulfonylhydrazides with thiols catalyzed by CuBr2 to afford thiosulfonates via a radical process is described.
Facile synthesis of symmetric thiosulfonates by oxidation of disulfide with oxone/MX (MX = KBr, KCl, NaBr and NaCl)
Natarajan, Palani
, p. 4131 - 4134 (2015/08/03)
Abstract A new method is described for the oxidation of aliphatic- and aromatic disulfides containing electron-donating and electron-withdrawing groups to their corresponding thiosulfonates using oxone in combination with the MX (MX = KBr, KCl, NaBr and NaCl). No obvious electronic effects influence the yields of thiosulfonates. Avoiding the usage of toxic and unstable reagents, mild reaction conditions, short reaction times and cost-effectiveness are advantages of this methodology when likened to known methods for thiosulfonates syntheses.
Sc(OTf)3-catalyzed synthesis of thiosulfonates in ionic liquid-water
Liang, Gaigai,Chen, Jing,Chen, Jiali,Li, Wanmei,Chen, Jiuxi,Wu, Huayue
supporting information, p. 6768 - 6770 (2013/01/15)
The first example of Sc(OTf)3-catalyzed sulfenylation of sodium sulfinates with N-(organothio)succinimides in ionic liquids (ILs) and water cosolvent system was developed, achieving thiosulfonates in moderate to excellent yields. Additionally, Sc(OTf)3/ILs could be recovered easily after the reactions and reused without a significant loss in the catalytic activity. Thus, the present protocol represents an interesting complement to known methods for thiosulfonates synthesis.
CO-OXIDATIONS OF SQUALENE WITH DISULFIDES AND THIOSULFINATES
Cole, Edward R.
, p. 147 - 160 (2007/10/02)
Comparison of the activities of alkyl and aryl disulfides in inhibiting the autoxidation of squalene show the greater efficiency of the alkyl derivatives.The effect of electron donating substituents in aryl derivatives, promoting efficiency in the order CH3O > CH3 > H, is reversed in the thiosulfinates when added directly, although they are considered to be inhibitors formed in situ from the disulfides.The anomaly is discussed in terms of rates of oxidation and stabilities of the oxidation products and leads to the concept of thiosulfinate/disulfide mixture as a more efficient antioxidant.Key words: Antioxidants; disulfides; thiosulfinates; sulfinyl group; stability.
