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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 1
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Original Articles

Ceric Ammonium Nitrate Oxidation: Tetracyclones

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Pages 79-80 | Received 11 Dec 1972, Published online: 06 Dec 2006
 

Abstract

In a previous publication1, we reported the study of ceric ammonium nitrate (CAN) oxidation of cyclic ketones. While ordinary ketones such as cyclohexanone, cyclopentanone, norbornanone furnished nitrato-carboxylic acids as the main products, adamantanone was uniquely oxidized to the corresponding lactone. We suggested that structurally constrained ketones would behave similarly, thus CAN oxidation may provide an alternative to the classical Baeyer-Villiger reaction2 which generally utilizes a peracid.

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