Module I Oxidation Reactions - NPTel

NPTEL – Chemistry – Reagents and Organic reactions
Applications
O 2N
O
CH 3CO 3H
AcOH, H 2SO 4
Scheme 13
Baeyer-Villiger oxidation has great synthetic applications as the reaction allows
the conversion of ketones to esters. The reaction works well with cyclic and
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O 2N
acyclic ketones (Scheme 14). For some examples, see:
MeO
O
CF 3CO 3H
Me
O MeCO3H O
AcOH
mCPBA
CH 2Cl 2
O
O
-Valerolactone
MeO
Scheme 14
Under these conditions, 1,2-diketones proceed reaction to give anhydride
(Scheme 15).
H 3C
O
O
CH 3
RCO 3H
Scheme 15
Me
O
O
O
O O
O
O
O
H 3C O CH 3
Baeyer-Villiger oxidation is a very useful protocol for the synthesis of large ring
lactones that are otherwise difficult to prepare by intramolecular esterification of
long-chain hydroxyacids (Scheme 16). For example, cyclopentadecanone can be
readily oxidized to the corresponding lactone in good yield.