text: More typically for laboratory operations, the Prilezhaev reaction is employed. This approach involves the oxidation of the alkene with a peroxyacid such as mCPBA. Illustrative is the epoxidation of styrene with perbenzoic acid to styrene oxide:
  The reaction proceeds via what is commonly known as the "Butterfly Mechanism". The peroxide is viewed as an electrophile, and the alkene a nucleophile. The reaction is considered to be concerted. The butterfly mechanism allows ideal positioning of the  sigma star orbital for  π electrons to attack. Because two bonds are broken and formed to the epoxide oxygen, this is formally an example of a coarctate transition state.
  Hydroperoxides are also employed in catalytic enantioselective epoxidations, such as the Sharpless epoxidation and the Jacobsen epoxidation. Together with the Shi epoxidation, these reactions are useful for the enantioselective synthesis of chiral epoxides. Oxaziridine reagents may also be used to generate epoxides from alkenes.