Wolff Rearrangement

Schematic representation of the Wolff Rearrangement.

Mechanism of the Wolff Rearrangement

Mechanism of the Wolff Rearrangement

Original publication	Angew. Chem. Int. Ed.. 1975, 14, 32.
Reviews	Chem. Rev.. 1994, 94, 1091. Comp. Org. Syn.. 1991, 3, 887. Eur. J. Org. Chem.. 2002, 0, 2193.

Sample reactions

intermediate structure

Et3N

hν

MeOH

RT, 3 h, 72%

intermediate structure

intermediate structure

Ag2O

MeOH

65 °C, , 69% (3 steps)

intermediate structure

intermediate structure

intermediate structure

NaHCO3

hν

H2O, THF

RT, 2 h, 90%

intermediate structure

intermediate structure

TMS2NH

hν

THF

RT, 6 h, 68% (3 steps)

intermediate structure

intermediate structure

AgNO3, NH3

EtOH, H2O

50 °C, 2.5 h

intermediate structure

intermediate structure

PhCO2Ag

H2O, THF

RT, 8 h, 41% (3 steps)

intermediate structure