Module I Oxidation Reactions - NPTel
Module I Oxidation Reactions - NPTel
Module I Oxidation Reactions - NPTel
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NPTEL – Chemistry – Reagents and Organic reactions<br />
2.1.3 Mn(IV) Reagents as an Oxidant<br />
MnO2 is a useful selective oxidizing reagent in organic synthesis. It is<br />
commercially available, and it can also be prepared by the reaction of<br />
MnSO4∙4H2O with KMnO4 in aqueous NaOH.<br />
G. Cahiez, M. Alami, Encyclopedia of Reagents for Organic Synthesis, John<br />
Wiley and Sons, Inc., L. A. Paquette Ed., New York, 1995, 5, 3229.<br />
2.1.3.1 <strong>Oxidation</strong> of Alcohols<br />
MnO2 can selectively oxidize allylic and benzylic alcohols to the corresponding<br />
carbonyl compounds (Scheme 7). The advantage of this method is that the<br />
reaction takes place under mild and neutral conditions, also carbon-carbon<br />
double and triple bonds are unaffected.<br />
OSiEt 3<br />
OH<br />
HO I<br />
Me Me Me Me<br />
Me<br />
HO<br />
CH 2OH<br />
Me<br />
Vitamin A (Retinol)<br />
OH<br />
OH<br />
MnO 2<br />
solvent free, rt<br />
MnO 2<br />
CH 2Cl 2<br />
MnO 2<br />
benzene<br />
MnO 2<br />
CHCl 3<br />
CH 2OH MnO 2<br />
Pentane, R.T.<br />
OHC<br />
CHO<br />
OSiEt 3<br />
Me Me Me Me<br />
Joint initiative of IITs and IISc – Funded by MHRD Page 18 of 122<br />
Me<br />
HO CHO<br />
CH 2OH<br />
Me<br />
Retinal<br />
O<br />
I<br />
CHO
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