Sulfides dioxirane epoxidation

Sugar-derived ketones, catalyzed dioxirane epoxidation, 1147 Sulfanilamide, TEARS assay, 667 Sulfate ion radical, peroxydisulfate organic salts, 1014 Sulfides... 

In general, peroxomonosulfates have fewer uses in organic chemistry than peroxodisulfates. However, the triple salt is used for oxidizing ketones (qv) to dioxiranes (7) (71,72), which in turn are useful oxidants in organic chemistry. Acetone in water is oxidized by triple salt to dimethyldioxirane, which in turn oxidizes alkenes to epoxides, polycycHc aromatic hydrocarbons to oxides and diones, amines to nitro compounds, sulfides to sulfoxides, phosphines to phosphine oxides, and alkanes to alcohols or carbonyl compounds. 

Dioxiranes, prepared from acetone and other aliphatic ketones by treatment with Oxone, can accomplish oxidations that are usually not achieved by Oxone itself [210, 211], Dioxiranes can be isolated by vacuum codistillation with the respective ketones [210], or else, they may be formed in situ and applied in the same reaction vessel [210, 211]. Examples of the applications of dioxiranes are epoxidations 210] and the oxidation of primary amines to nitro compounds [211], of tertiary amines to amine oxides [210], and of sulfides to sulfoxides [210] (equation 12). 

---