Temperature, Solvent, and Substituent Effects on the Singlet Oxidations of Allylic Phenyl Sulfoxides, Sulfones, and Sulfides

Article abstract of DOI:10.1021/ja00203a023

The reaction of singlet oxygen with a series of allylic sulfoxides, sulfones, and sulfides have been examined as a function of extent of reaction, temperature, and solvent.Hydroperoxy groups but not alkyl, hydrogen, or hydroxyl on chiral carbons β to sulfide sulfur induce diastereoselective sulfoxide formations.Evidence is presented that suggests that the oxidation at sulfur occurs with anchimeric assistance from the hydroperoxy group via a favorable sulfurane-like transition state.