The Synthesis of Some Compounds Containing the Selenocarbonyl Group by Using Viehe's Salt/Sodium Hydrogen Selenide: an Approach to Cyclic Selenocarbonates in the Monosaccharide Series

Abstract

The treatment of various thiols, phenols and amines with Viehe's salt (Me₂N⁺=CCl₂ Cl ^-), followed by addition to sodium hydrogen selenide in ethanol, can lead to useful syntheses of compounds containing the selenocarbonyl group, namely selenothiocarbamates, selenodithiocarbonates, selenothiocarbonates and selenoureas . As well, the combination of Viehe's salt/sodium hydrogen selenide allows the conversion of some carbohydrate cis vicinal diols into novel cyclic selenocarbonates, and a single-crystal X-ray diffraction structure determination of one of these selenocarbonates is reported. The treatment of these selenocarbonates with methyl iodide and various phosphorus reagents is reported, as well as some unsuccessful attempts towards tellurocarbonates and telluroureas.