ChemInform Abstract: Role of Hexafluoro-2-propanol in Selective Oxidation of Sulfide to Sulfoxide: Efficient Preparation of Glycosyl Sulfoxides.
Abstract
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ChemInform Abstract
H2O2/hexafluoro-2-propanol is found to be a facile, selective, and efficient oxidant for the conversion of sulfides to sulfoxides. C=C double bonds and nitrogen atoms are not affected by this reagent system. The oxidation of glycosyl sulfides to the corresponding sulfoxides is achieved in high yields without affecting the protecting groups. Hexafluoro-2-propanol forms strong hydrogen bond with H2O2 thus activating the hydroxy group and forms hydrogen bond with the oxygen atom of the sulfoxide which leads to decrease of nucleophilicity at the sulfur atom.
