The reaction conditions are compatible with acetals, acetates and benzoates. However, formate can be oxidized as free alcohol to give ketone. The oxidation of equatorial hydroxyl groups are favored compared to the axial hydroxyl groups (Scheme 9).
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Scheme 9 |
Mechanism
The reaction is performed by refluxing a secondary alcohol with acetone in the presence of Al(OiPr)3. The latter serves only to form the aluminium alkoxide of the alcohol that is oxidized through a cyclic transition state at the expense of acetone to a ketone and 2-propanol.
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