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Module I Oxidation Reactions - NPTel

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NPTEL – Chemistry – Reagents and Organic reactions<br />

1.3.9 <strong>Oxidation</strong> of Aromatic Ring<br />

Chromium based reagents are extensively used for the partial oxidation of cyclic<br />

hydrocarbons to the quinones (Scheme 14).<br />

CH 3<br />

CrO 3<br />

AcOH<br />

CrO 3<br />

AcOH<br />

1.3.10 Asymmetric Epoxidation<br />

Scheme 14<br />

Joint initiative of IITs and IISc – Funded by MHRD Page 34 of 122<br />

O<br />

O<br />

Menadione<br />

O<br />

CH 3<br />

O<br />

Anthraquinone<br />

Chiral chromium(VI)-salen complex has been studied for asymmetric epoxidation<br />

of trans alkenes (Scheme 15). The reaction works in both catalytic and<br />

stoichiometric mode but the stoichiometric mode works slightly well than catalytic<br />

mode.<br />

Ph<br />

Me<br />

Catalyst,<br />

PhIO<br />

MeCN, 0 C Ph<br />

O<br />

Me<br />

Scheme 15<br />

CF 3<br />

N O<br />

Cr<br />

N<br />

O L O<br />

Catalyst<br />

L = Ph 3PO<br />

F 3C<br />

NO 3

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