KMnO4 oxidation mechanism

PeetPb

Hi,
I've been searching for the oxidation mechanism of KMnO4 on alkanes (aryl derivatives like toluene). All I found was some web sites telling me the overall reaction and that the mechanism is either unimportant or too complicated for their purposes. I found some little notes that it has a radical character something like the MnO4 anion removes the hydrogens from the methyl group of toluene and leaves a free radical. Beyond that I couldn't get anything. Please if you can tell me the reaction mechanism I'd be very happy ...

thanx

ChiralWaltz

wiki- toluene

"With other reagents the methyl side chain in toluene may react, undergoing oxidation. Reaction with potassium permanganate and diluted acid (e.g., sulfuric acid) or potassium permanganate with concentrated sulfuric acid, leads to benzoic acid"

here are some notes:
faculty.philau.edu/milkevitchm/Microscale_Oxid_Toluene.ppt

and another
phs244.wikispaces.com/file/view/Side+chain.pptx

I haven't played with those types of reactions yet so I'm not sure how helpful this will be. Look for "oxidation of side chains"