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 />
sensitive groups. The powdered NaOAc is used along with PCC for the oxidation<br />
of the substrate containing acid labile groups. PCC is commercially available and<br />
could also be prepared.<br />
N<br />
H<br />
O<br />
O Cr<br />
O<br />
PCC<br />
G. Piancatelli,, Encylopedia of Reagents for Organic Synthesis, John Wiley and<br />
Sons, Inc., L. A. Paquette, Ed., New York, 1995, 6, 4356.<br />
<strong>Oxidation</strong> of Alcohols<br />
HO<br />
Me<br />
H<br />
Me<br />
Me<br />
Me<br />
H<br />
CO 2Me<br />
H<br />
OH PCC<br />
CH 2Cl 2, rt<br />
Joint initiative of IITs and IISc – Funded by MHRD Page 28 of 122<br />
Cl<br />
PCC<br />
O<br />
R OH<br />
CH2Cl2, rt<br />
R H<br />
OH<br />
H<br />
O<br />
Me<br />
H OTBDMS<br />
PCC<br />
CH 2Cl 2, rt<br />
PCC<br />
CH 2Cl 2, rt<br />
Scheme 3<br />
H<br />
Me<br />
H<br />
Me<br />
Me<br />
O<br />
O<br />
H<br />
Me<br />
H<br />
CO 2Me<br />
O<br />
H<br />
O<br />
H<br />
Me<br />
H OTBDMS<br />
Another important use of PCC is the transformation of allylic tertiary alcohols to<br />
α,β-unsaturated ketones (Scheme 4). This reaction is thought to proceed via a<br />
[3,3]-sigmatropic rearrangement of allylic chromate ester to give new allylic
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