Rubottom Oxidation

Schematic representation of the Rubottom Oxidation.
Mechanism of the Rubottom Oxidation
Mechanism of the Rubottom Oxidation
Sample reactions
intermediate structure
mCPBA
Hexane(s)
RT, 5 h, 74%
intermediate structure
intermediate structure
Camphorsulfonic acid
Acetone
RT, 30 min, 89% (3 steps)
intermediate structure
intermediate structure
mCPBA, NaHCO3
CH2Cl2
0 °C, 30 min, 96% (2 steps)
intermediate structure
intermediate structure
mCPBA, NaHCO3, HF
PhMe, THF
-10 to 0 °C, , 66% (3 steps)
intermediate structure
intermediate structure
mCPBA
MeOH
0 °C, 30 min, 91%
intermediate structure
intermediate structure
DMDO
CH2Cl2, MeOH
-40 °C, 15 min, 76% (2 steps)
intermediate structure
intermediate structure
mCPBA, NaHCO3
CH2Cl2, H2O
0 °C, , 66% (2 steps)
intermediate structure