Criegee Reaction

Schematic representation of the Criegee Reaction.

Mechanism of the Criegee Reaction

Mechanism of the Criegee Reaction

Original publication	Ber. Dtsch. Chem. Ges.. 1931, 64, 260. J. Org. Chem.. 1986, 51, 789.
Review

Sample reactions

intermediate structure

Pb(OAc)4

AcOH, CH2Cl2

-20 °C, 10 min, 71% (2 steps)

intermediate structure

intermediate structure

Pb(OAc)4

PhH

20 min

intermediate structure

intermediate structure

Na2CO3, Pb(OAc)4

CH2Cl2

0 °C to RT, 2.5 h

intermediate structure

intermediate structure

Pb(OAc)4

MeOH, PhH

0 °C, 10 min, 97%

intermediate structure

intermediate structure

Pb(OAc)4

MeOH, PhH

0 °C, 5 min, 61% (2 steps)

intermediate structure

intermediate structure

Pb(OAc)4

CH2Cl2

-78 to 0 °C, 30 min, 69% (2 steps)

intermediate structure

intermediate structure

Pb(OAc)4

MeOH, PhH

0 °C, 10 min

intermediate structure