Fully fluorinated alkoxides. Part IV. Derivatives of perfluoropinacol

Abstract

The reductive dimerization of hexafluoroacetone, by reaction with sodium in a donor solvent, leads to the ionic disodium alkoxide of perfluoropinacol, a valuable intermediate for the preparation of pinacol derivatives. Cyclic alkoxides of silicon, germanium, tin, and boron are made by the reaction of this disodium alkoxide with various dihalides.Reaction with thionyl chloride, sulfuryl chloride, or sulfur(II) chloride gives perfluoropinacol sulfite, sulfate, and ortho-sulfite. respectively. The stereochemistry of the last compound is discussed.