Rubottom Oxidation

Schematic representation of the Rubottom Oxidation.

Mechanism of the Rubottom Oxidation

Mechanism of the Rubottom Oxidation

Original publication	Tetrahedron Lett.. 1974, 15, 4319.
Reviews	Adv. Synth. Catal.. 2004, 346, 143. Org. React.. 2003, 62, 1.

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

HF, mCPBA, NaHCO3

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