Front Cover: Dialkyl Dicyanofumarates as Oxidizing Reagents for the Conversion of Thiols into Disulfides and Selenols into Diselenides (Eur. J. Org. Chem. 46/2017). Issue 46 (21st November 2017)

• Record Type: Journal Article
• Authors: Mlostoń, Grzegorz; Capperucci, Antonella; Tanini, Damiano; Hamera‐Fałdyga, Róża; Heimgartner, Heinz
• Is Part Of: European journal of organic chemistry. Issue 46(2017)
• Page Start: 6815
• Page End: 6815
• Publication Date: 2017-11-21
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701597
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The Front Cover shows the novel, high‐yielding conversion of thiols and selenols into symmetrical disulfides and diselenides, respectively, which takes place under mild conditions in the presence of diethyl dicyanofumarate as an oxidizing agent. The latter is converted into a 1:1 mixture of diastereoisomeric meso ‐ andDL ‐diethyl 2, 3‐dicyanosuccinates. The reactions are of great interest also from a mechanistic point of view and are believed to occur via a cascade single‐electron transfer (SET) redox reaction. The waterfall perfectly reflects the step‐wise nature of the processes, leading to the formation of the S–S or Se–Se bonds. A remarkable switch of the reaction course occurs: instead of the expected thia‐Michael addition, a redox reaction takes place. It is initiated by an electron transfer from the –SH (or –SeH) group to the strongly electron‐deficient C=C bond. More information can be found in theFull Paper by G. Mlostoń, A. Capperucci et al.