Semi-Pinacol Rearrangement

Schematic representation of the Semi-Pinacol Rearrangement.
Mechanism of the Semi-Pinacol Rearrangement
Mechanism of the Semi-Pinacol Rearrangement
Sample reactions
intermediate structure
AlMe3
CH2Cl2
-78 °C, 60 min, 75% (2 steps)
intermediate structure
intermediate structure
BF3.OEt2
THF
92%
intermediate structure
intermediate structure
LiBr, HMPA
PhMe
Reflux, 35 min
intermediate structure
intermediate structure
LiBr, HMPA
PhMe
Reflux, 2 h
intermediate structure intermediate structure