1.9.3  Dioxiranes

Dialkyl dioxiranes are versatile oxidizing agents that can be produced from oxone (potassium peroxymonosulfate) and ketones. Dioxiranes are extensively used for the epoxidation of alkenes (Scheme 3).

Scheme 6

If the ketones are chiral, chiral dioxiranes can be generated, which can be used as an effective chiral reagent for asymmetric epoxidation of alkenes with excellent enantioselectivity (Scheme 7).

Scheme 7

J. M. Crandall, Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons, Inc., L. A. Paquette, Ed., New York, 1995, 6, 4265.