Chemistry of Dioxiranes. 6. Electronic Effects in the Oxidation of Sulfides and Sulfoxides by Dimethyldioxirane

Article abstract of DOI:10.1021/jo00381a007

Dimethyldioxirane (1) oxidizes a series of aryl methyl sulfides to the corresponding sulfoxides.In a separate series of reactions the sulfoxides were oxidized by 1 to the corresponding sulfones.The relative rates of oxidation in both series were treated with the Hammett ρ? relationship.The oxidations were found to be electrophilic in character with ρ values for the sulfide and sulfoxide oxidations equal to -0.77 and -0.76, respectively.