Divergent decomposition pathways of DMSO mediated by solvents and additives

IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Sulfur Chemistry Pub Date : 2024-05-03 DOI:10.1080/17415993.2023.2280671
Kaishuo Zhao , Zilin Fang , Shuai Peng , Xixuan Zhao , Yongguo Liu , Baoguo Sun , Hongyu Tian , Sen Liang
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Abstract

DMSO (dimethyl sulfoxide) plays an increasingly significant role in various synthetic processes by generating diverse active intermediates in situ, which actively participate in reactions. It is crucial to control the formation of these active intermediates to prevent their mutual interference during utilization. Our previous research identified methyl methanethiosulfonate (MMTS) as a major decomposition product of DMSO when catalyzed by small amounts of (COCl)2 in CH3CN. In the current study, we investigated how different solvents and additives can mediate the formation of MMTS. Complete avoidance of MMTS formation was achieved in 1,4-dioxane, while only trace amounts were observed in toluene, MTHF, or CHCl3. Moreover, the decomposition pathway of DMSO in these solvents was effectively mediated through the addition of strong acids (HX, where X = TfO, ClO4, I, Br, or Cl) or in the presence of LiI, CH3I, or Br2. The effects of solvents and additives on the decomposition of DMSO were explored. The possible mechanisms for the decomposition of DMSO under different conditions were proposed and discussed.

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二甲基亚砜在溶剂和添加剂作用下的不同分解途径
二甲基亚砜(DMSO)在各种合成过程中发挥着越来越重要的作用,它能在原位生成各种活性中间体,积极参与反应。控制这些活性中间体的形成以防止它们在利用过程中相互干扰至关重要。我们之前的研究发现,在 CH3CN 中的少量 (COCl)2 催化下,甲硫磺酸甲酯(MMTS)是二甲基亚砜的主要分解产物。在本研究中,我们探讨了不同溶剂和添加剂如何介导 MMTS 的形成。在 1,4-二氧六环中完全避免了 MMTS 的形成,而在甲苯、MTHF 或 CHCl3 中仅观察到微量的 MMTS。此外,通过添加强酸(HX,其中 X = TfO、ClO4、I、Br 或 Cl)或在 LiI、CH3I 或 Br2 的存在下,DMSO 在这些溶剂中的分解途径得到了有效的调解。探讨了溶剂和添加剂对二甲基亚砜分解的影响。提出并讨论了二甲基亚砜在不同条件下分解的可能机制。
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来源期刊
Journal of Sulfur Chemistry
Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
4.10
自引率
9.10%
发文量
38
审稿时长
6-12 weeks
期刊介绍: The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.
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