Prilezhaev reaction

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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.[1] 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.[2] An illustrative example is the epoxidation of styrene with perbenzoic acid to styrene oxide:[3]

Prilezhaev Reaction

Reaction mechanism[edit]

The reaction proceeds via what is commonly known as the "Butterfly Mechanism."[4] 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.[5]

Butterfly Mechanism

References[edit]

  1. ^ Nikolaus Prileschajew (1909). "Oxydation ungesättigter Verbindungen mittels organischer Superoxyde". Berichte der deutschen chemischen Gesellschaft. 42 (4): 4811–4815. doi:10.1002/cber.190904204100. 
  2. ^ László Kürti and Barbara Czakó. (2005). Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms. Elsevier Academic Press. p. 362. ISBN 0124297854. 
  3. ^ Harold Hibbert and Pauline Burt (1941). "Styrene Oxide". Org. Synth. ; Coll. Vol., 1, p. 494 
  4. ^ Paul D. Bartlett (1950). "Recent work on the mechanisms of peroxide reactions". Record of Chemical Progress. 11: 47–51. 
  5. ^ John O. Edwards (1962). Peroxide Reaction Mechanisms. Interscience, New York. pp. 67–106.