Deprotection and Oxidation of Alcohols to Ketones

The sensitivity of some alcohol protecting groups to the acidic conditions of Jones oxidation allow the operation of one-pot reactions, in which deprotection of alcohols is followed by in situ oxidation to ketones. Some interesting synthetic applications of this principle are listed bellow  

26a The THP ether is hydrolysed and oxidized to ketone under Jones conditions.  

The TBDPS ether remains unaffected, while the more acid-sensitive TMS ether is hydrolysed and the corresponding alcohol is oxidized to ketone. 

The deprotection of the TBS ethers—with the corresponding oxidation to ketones or carboxylic acids—can be purposefully facilitated by the addition of some hydrofluoric acid65 or KF66 to the Jones reaction mixture. 

The TBS group is removed with the assistance of potassium fluoride added to  

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