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 />
Mechanism<br />
O<br />
base<br />
Examples<br />
Me<br />
Me<br />
CO 2Et<br />
H<br />
O<br />
SeO 2, EtOH<br />
Ph Se Br<br />
Me<br />
HOH 2C<br />
CO 2Et<br />
H<br />
Yield: 90%<br />
Joint initiative of IITs and IISc – Funded by MHRD Page 40 of 122<br />
O<br />
Se<br />
Ph oxidation<br />
R. W. Curley, Jr., C. J. Thomas, J. Org. Chem. 1986, 51, 256.<br />
Me Me<br />
SeO 2<br />
Me CH 2OH<br />
>98% this isomer<br />
H. Rapoport, U. T. Bhalerao, J. Am. Chem. Soc. 1971, 93, 4835.<br />
1.4.2 <strong>Oxidation</strong> of Alcohols with Aluminium Alkoxides<br />
(Oppenauer <strong>Oxidation</strong>)<br />
O<br />
Ph<br />
Se<br />
O<br />
Aluminium triisopropoxide and aluminium tributoxide have been found to be<br />
effective reagents for the oxidation of secondary alcohols to ketones in the<br />
presence of ketone such as acetone. Acetone acts as a hydrogen acceptor, and<br />
it is transformed into 2-propanol. The presence of excess of acetone drives the<br />
reaction towards the oxidation product. The use of inert solvent such as benzene,<br />
toluene or dioxane minimizes the side products and also helps to raise the<br />
reaction temperature.<br />
H<br />
O
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