Oppenauer Oxidation isthe process of conversion of secondary alcohols to
ketones by selective oxidation. This reaction is named after Rupert Viktor
Oppenauer. Oxidation reaction takes place in the presence of [Al(i-Pro)3] in excess
of acetone.
It is an aluminium alkoxide catalysed oxidation of a secondary alcohol to the
corresponding ketone. This is the reverse of the Meerwein Ponndorf Verley
reduction. It is a very good method to oxidise allylic alcohols to α, β- unsaturated
ketones.
CH3
H3C
O
R2
R1
OH
R2
R1
O
CH3
H3C
OH
Al(i-PrO)3 /heat
INTRODUCTION
3.
There are fivesteps---
1.In the first step, alcohol coordinates with aluminium isopropoxide to form
a complex
2.This complex reacts with a ketone to form a six-membered transition
complex
3.The alpha-carbon of the alcohol is converted to the carbonyl carbon from
the aluminium-catalysed hydride shift.
4.The acetone proceeds over a six-membered transition state.
5.The desired ketone is formed after the hydride transfer
Oppenauer Oxidation Mechanism