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Showing papers on "Oxidation of secondary alcohols to ketones published in 1984"


Journal ArticleDOI
TL;DR: In this article, hydrogen peroxide in conjunction with ammonium molybdate effects the epoxidation of olefins, the oxidation of secondary alcohols to ketones, and the oxidization of aldehydes to acids.
Abstract: Hydrogen peroxide in conjunction with ammonium molybdate effects the epoxidation of olefins, the oxidation of secondary alcohols to ketones, and the oxidation of aldehydes to acids. By controlling pH olefin epoxidation can be suppressed in favor of alcohol oxidation. Secondary alcohols are cleanly oxidized in the presence of primary alcohols. Sterically more hindered alcohols are oxidized more rapidly than less hindered alcohols. The latter rate preference permitted selective conversion of a 17-hydroxyl group of several steroids into a.ketone in the presence of a 3-hydroxyl group. The chemoselective oxidation of aldehydes to carboxylic acids is another use of this inexpensive oxidation system. A rate acceleration by addition of the lanthanide salt cerium chloride is noted and attributed to enhanced rates of hydration of the aldehyde. Potential mechanisms are discussed.

35 citations


Journal ArticleDOI
TL;DR: In this article, hydrogen peroxide in conjunction with ammonium molybdate effects the epoxidation of olefins, the oxidation of secondary alcohols to ketones, and the oxidization of aldehydes to acids.
Abstract: Hydrogen peroxide in conjunction with ammonium molybdate effects the epoxidation of olefins, the oxidation of secondary alcohols to ketones, and the oxidation of aldehydes to acids. By controlling pH olefin epoxidation can be suppressed in favor of alcohol oxidation. Secondary alcohols are cleanly oxidized in the presence of primary alcohols. Sterically more hindered alcohols are oxidized more rapidly than less hindered alcohols. The latter rate preference permitted selective conversion of a 17-hydroxyl group of several steroids into a.ketone in the presence of a 3-hydroxyl group. The chemoselective oxidation of aldehydes to carboxylic acids is another use of this inexpensive oxidation system. A rate acceleration by addition of the lanthanide salt cerium chloride is noted and attributed to enhanced rates of hydration of the aldehyde. Potential mechanisms are discussed.