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 />
electron withdrawing substituent exhibits greater reactivity compared to that<br />
containing electron donating group. For an example, m-CPBA is more reactive<br />
compared to PhCO3H.<br />
OMe<br />
O<br />
Ph Ph<br />
Ph<br />
Ph<br />
Me<br />
Me<br />
Me<br />
mCPBA<br />
mCPBA<br />
Scheme 2<br />
mCPBA<br />
CHCl 3<br />
mCPBA<br />
CH 2Cl 2<br />
Scheme 3<br />
Joint initiative of IITs and IISc – Funded by MHRD Page 46 of 122<br />
O<br />
Ph Ph<br />
cis-epoxide<br />
Ph<br />
O<br />
Ph<br />
trans-epoxide<br />
Me<br />
O<br />
Me<br />
OMe<br />
In case of cyclic alkenes that are conformationally rigid, the reagent approaches<br />
from the less hindered side of the double bond. This is illustrated in the oxidation<br />
of norbornene (Scheme 4).<br />
PhCO 3H<br />
CHCl 3<br />
Scheme 4<br />
H<br />
H<br />
95%<br />
O<br />
+<br />
O<br />
5%<br />
H<br />
O<br />
O<br />
H<br />
Me
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