Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties

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.

Keywords: Fluorine; Oxidation; Selenium; Selenones; Selenoximines.