Premium
Front Cover: Dialkyl Dicyanofumarates as Oxidizing Reagents for the Conversion of Thiols into Disulfides and Selenols into Diselenides (Eur. J. Org. Chem. 46/2017)
Author(s) -
Mlostoń Grzegorz,
Capperucci Antonella,
Tanini Damiano,
HameraFałdyga Róża,
Heimgartner Heinz
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701597
Subject(s) - chemistry , oxidizing agent , reagent , redox , front cover , electron transfer , combinatorial chemistry , photochemistry , cover (algebra) , organic chemistry , mechanical engineering , engineering
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 ‐ and DL ‐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 the Full Paper by G. Mlostoń, A. Capperucci et al.