Oxidative Cleavage of Ethers by Metallic Nitrates Supported on Silica Gel

Abstract

Metallic nitrates supported on silica gel efficiently cleave and oxidize ethers to the corresponding aldehydes or ketones under mild conditions. Silica gel is essential for the efficient oxidation, and Cu(No3)2and Zn(No3)2are suitable for practical use. Overoxidation of the product aldehydes is not observed. In some cases alkyl nitrites are isolated in addition to the carbonyl compounds, and the decomposition of alkyl nitrites to the corresponding carbonyl compounds is promoted by the presence of metallic nitrates supported on silica gel. Mechanistic study suggests nitrogen dioxide is an active species. © 1990, American Chemical Society. All rights reserved.