Xixuan Zhao , Hao Wang , Shuting Yin , Shuai Peng , Fengjiao Li , Qian Zhang , Yongguo Liu , Baoguo Sun , Hongyu Tian , Sen Liang
{"title":"用二甲基亚砜对硫醇和 β-二羰基进行甲磺化反应","authors":"Xixuan Zhao , Hao Wang , Shuting Yin , Shuai Peng , Fengjiao Li , Qian Zhang , Yongguo Liu , Baoguo Sun , Hongyu Tian , Sen Liang","doi":"10.1080/17415993.2023.2290269","DOIUrl":null,"url":null,"abstract":"<div><p>The methanesulfenylation of various mercaptans and β-dicarbonyls has been investigated using in-situ generated methyl methanethiosulfonate (MMTS) from DMSO, facilitated by a catalytic amount of (COCl)<sub>2</sub>. Employing the MMTS solution alongside Et<sub>3</sub>N led to the synthesis of a range of unsymmetrical disulfides with good yields. Furthermore, the introduction of [<sup>2</sup>H<sub>6</sub>]-DMSO enabled the successful preparation of various [<sup>2</sup>H<sub>3</sub>]-disulfides. In the case of most β-dicarbonyls, successful methanesulfenylation was accomplished using Et<sub>3</sub>N and DBU, resulting in favorable yields.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 3","pages":"Pages 330-345"},"PeriodicalIF":2.1000,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Methanesulfenylation of mercaptans and β-dicarbonyls with DMSO\",\"authors\":\"Xixuan Zhao , Hao Wang , Shuting Yin , Shuai Peng , Fengjiao Li , Qian Zhang , Yongguo Liu , Baoguo Sun , Hongyu Tian , Sen Liang\",\"doi\":\"10.1080/17415993.2023.2290269\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The methanesulfenylation of various mercaptans and β-dicarbonyls has been investigated using in-situ generated methyl methanethiosulfonate (MMTS) from DMSO, facilitated by a catalytic amount of (COCl)<sub>2</sub>. Employing the MMTS solution alongside Et<sub>3</sub>N led to the synthesis of a range of unsymmetrical disulfides with good yields. Furthermore, the introduction of [<sup>2</sup>H<sub>6</sub>]-DMSO enabled the successful preparation of various [<sup>2</sup>H<sub>3</sub>]-disulfides. In the case of most β-dicarbonyls, successful methanesulfenylation was accomplished using Et<sub>3</sub>N and DBU, resulting in favorable yields.</p></div>\",\"PeriodicalId\":17081,\"journal\":{\"name\":\"Journal of Sulfur Chemistry\",\"volume\":\"45 3\",\"pages\":\"Pages 330-345\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-05-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Sulfur Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1741599323001046\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Sulfur Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1741599323001046","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Methanesulfenylation of mercaptans and β-dicarbonyls with DMSO
The methanesulfenylation of various mercaptans and β-dicarbonyls has been investigated using in-situ generated methyl methanethiosulfonate (MMTS) from DMSO, facilitated by a catalytic amount of (COCl)2. Employing the MMTS solution alongside Et3N led to the synthesis of a range of unsymmetrical disulfides with good yields. Furthermore, the introduction of [2H6]-DMSO enabled the successful preparation of various [2H3]-disulfides. In the case of most β-dicarbonyls, successful methanesulfenylation was accomplished using Et3N and DBU, resulting in favorable yields.
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.