Dioxiranes may be produced through the action of KHSO on carbonyl compounds. Because of their low-lying σ* orbital, they are highly electrophilic oxidants and react with unsaturated functional groups, Y-H bonds (yielding oxygen insertion products), and heteroatoms. The most common dioxiranes employed for organic synthesis are dimethyldioxirane (DMD) and trifluoromethyl-methyldioxirane (TFD). The latter is effective for chemoselective oxidations of C-H and Si-H bonds. Although this class of reagents is most famous for the epoxidation of alkenes, dioxiranes have been used extensively for other kinds of oxidations as well.