Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties
Arnaud de Zordo‐Banliat, Kévin Grollier, Nicolas Vanthuyne, Sébastien Floquet, Thierry Billard, Guillaume Dagousset, Bruce Pégot, Emmanuel Magnier
Abstract
Abstract A selective access to perfluoroalkyl selenoxides, via Oxone® as oxidant or to selenones by using a Polyoxometalate‐based Ionic Liquid (POM‐IL) as a catalyst for the oxidation step is described. The reaction works with various perfluoralkyl chains and substituents with satisfactory to excellent yields. A two‐step one‐pot reaction from selenocyanates was performed to gain access to perfluoroalkyl selenoxides. The previously unknown perfluoroalkyl selenoximines family was also prepared with good yields. Having unlocked two strategies for the synthesis of fluoroalkylated Se IV and Se VI compounds, we then evaluated the Hansch‐Leo lipophilicity parameters of these groups. Finally, asymmetric aryl perfluoroalkyl selenoximines were resolved to determine their absolute configurations.