Extended Pummerer fragmentation mediated by carbon dioxide and cyanide
| Autor: | Jian Liu, Fadhil S. Kamounah, Rasmus Refsgaard Kragh, Ji-Woong Lee |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Reaction mechanism
010405 organic chemistry Pummerer rearrangement Cyanide Organic Chemistry chemistry.chemical_element Sulfoxide 010402 general chemistry Photochemistry 01 natural sciences Biochemistry Sulfur 0104 chemical sciences chemistry.chemical_compound chemistry Oxidation state Reagent Drug Discovery Carbon dioxide |
| Zdroj: | Tetrahedron. 76:131633 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2020.131633 |
| Popis: | Pummerer rearrangement reactions generate sulfur (II) oxidation state from sulfur (IV) starting materials in the presence of activating reagents. We found unprecedented transformation of vinyl sulfoxide; disulfide formation reactions mediated by atmospheric pressure of carbon dioxide in extended Pummerer rearrangement reactions. Only under CO2 atmosphere, we observed moderate to high yields of disulfide starting from sulfur (IV) starting materials. Investigations on the reaction mechanism revealed that the degradation of the starting materials and the products was significant in the absence of CO2. Further evidence for the suggested reaction mechanism was obtained by a cross-over experiment and a radical trapping reagent. |
| Databáze: | OpenAIRE |
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