Prilezhaev reaction

Prilezhaev reaction
Named after	Nikolaus Prileschajew
Reaction type	Ring forming reaction
Identifiers
Organic Chemistry Portal	prilezhaev-reaction
RSC ontology ID	RXNO:0000405

The Prilezhaev reaction, also known as the Prileschajew reaction or Prilezhaev epoxidation, is the chemical reaction of an alkene with a peroxy acid to form epoxides. It is named after Nikolaus Prileschajew, who first reported this reaction in 1909. The most widely used peroxy acid for oxidation of the alkene is m-CPBA, due to its stability and good solubility in most organic solvents. An illustrative example 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 numbers in the mechanism below are for simplification). The butterfly mechanism allows ideal positioning of the O-O sigma star orbital for C-C Pi electrons to attack.

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