Dioxirane epoxidation is highly versatile, and compares favorably to related peracid oxidations in many respects. Peracids generate acidic byproducts, meaning that acid-labile substrates and products must be avoided. Dioxirane epoxidations using isolated oxidant can be carried out under neutral conditions without the need for aqueous buffering. However, catalytic dioxirane oxidations do require water and are not suitable for hydrolytically unstable substrates.
Some methods are well-suited to the oxidation of electron-rich or electron-poor double bonds, but few are as effective for both classes of substrate as dioxiranes. Weitz-Scheffer conditions (NaOCl, HO/KOH, tBuOH/KOH) work well for oxidations of electron-poor double bonds, and sulfonyl-substituted oxaziridines are effective for electron-rich double bonds.
Metal-based oxidants are often more efficient than dioxirane oxidations in the catalytic mode; however, environmentally unfriendly byproducts are typically generated. In the realm of asymmetric methods, both the Sharpless epoxidation and Jacobsen epoxidation surpass asymmetric dioxirane oxidations in enantioselectivity. Additionally, enzymatic epoxidations are more enantioselective than dioxirane-based methods; however, operational difficulties and low yields are sometimes associated with enzymatic oxidations