{"title":"Exploring Divergent Role of Amine in Chemodivergent Synthesis of 4-Alkyl/Aryl-3H-1,2-Dithiole-3-Thione and Ketothioamide","authors":"Ankush Gupta, Guddeangadi N. Gururaja","doi":"10.1002/chem.202404346","DOIUrl":null,"url":null,"abstract":"<p>The selective synthesis of 4-alkyl/aryl-<i>3H</i>-1,2-dithiole-3-thione in THF and water-dependent switchable product ketothioamide is demonstrated. The presented method describes explicitly the synthesis of the extremely rare positional isomer 4-alkyl/aryl-<i>3H</i>-1,2-dithiole-3-thione, a unique structure distinct from another positional isomer, 5-alkyl/aryl-<i>3H</i>-1,2-dithiole-3-thione. The unique umpolung of the nitromethyl group is exploited for solvent-selective nucleophilic sulfur and amine addition. The dual role of the -CBr<sub>3</sub> moiety in the substrate as both a synthetic equivalent and an eliminating group is demonstrated.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":"31 12","pages":""},"PeriodicalIF":3.7000,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - A European Journal","FirstCategoryId":"92","ListUrlMain":"https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202404346","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The selective synthesis of 4-alkyl/aryl-3H-1,2-dithiole-3-thione in THF and water-dependent switchable product ketothioamide is demonstrated. The presented method describes explicitly the synthesis of the extremely rare positional isomer 4-alkyl/aryl-3H-1,2-dithiole-3-thione, a unique structure distinct from another positional isomer, 5-alkyl/aryl-3H-1,2-dithiole-3-thione. The unique umpolung of the nitromethyl group is exploited for solvent-selective nucleophilic sulfur and amine addition. The dual role of the -CBr3 moiety in the substrate as both a synthetic equivalent and an eliminating group is demonstrated.
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Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields.
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