Convenient transformation of thioamides and thioketones to their oxygen analogues with singlet oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate
{"title":"Convenient transformation of thioamides and thioketones to their oxygen analogues with singlet oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate","authors":"","doi":"10.1080/17415993.2024.2337841","DOIUrl":null,"url":null,"abstract":"<div><p>An efficient method for the oxidative transformation of thioamides and thioketones to their oxygen analogues with singlet oxygen is reported. Singlet oxygen was produced in situ from the fragmentation of the trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate in the presence of KOH, and it has been explored as an effective oxidant for oxidative desulfurization of thioamides and thioketones. This protocol provides amides and ketones in excellent yields (80–90%) at room temperature under mild conditions. The thioamides reacted very well with this reagent system. The conjugation of neighboring NH and C=S groups appears to enhance yields for thioamides. Further investigation showed that this reagent system is also an efficient system for deprotection of thionoesters to esters.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 4","pages":"Pages 490-499"},"PeriodicalIF":2.1000,"publicationDate":"2024-07-03","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/S1741599324000102","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
An efficient method for the oxidative transformation of thioamides and thioketones to their oxygen analogues with singlet oxygen is reported. Singlet oxygen was produced in situ from the fragmentation of the trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate in the presence of KOH, and it has been explored as an effective oxidant for oxidative desulfurization of thioamides and thioketones. This protocol provides amides and ketones in excellent yields (80–90%) at room temperature under mild conditions. The thioamides reacted very well with this reagent system. The conjugation of neighboring NH and C=S groups appears to enhance yields for thioamides. Further investigation showed that this reagent system is also an efficient system for deprotection of thionoesters to esters.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
