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Showing papers on "Oxidation of secondary alcohols to ketones published in 1971"


Book ChapterDOI
TL;DR: The use of a two phase ether-aqueous chromic acid system for oxidation of secondary alcohols to ketones has been reported to afford, in a rapid fashion, ketones that are remarkably free of isomerized and side products as mentioned in this paper.
Abstract: Publisher Summary This chapter presents an overview of the reactions that are of special interest in medicinal chemistry. The use of a two phase ether-aqueous chromic acid system for oxidation of secondary alcohols to ketones has been reported to afford, in a rapid fashion, ketones that are remarkably free of isomerized and side products. Amine oxides can be prepared in 90% yield from the corresponding mines, using m-chloroperbenzoic acid in chloroform, followed by purification of the reaction mixture on an alumina column. In other studies, electrolysis has been reported to effect the selective hydrogenolysis of aryl bromide moieties in the presence of other reducible groups. The yield was 94%, compared to 13% with Et 3 SnH. Amides may also be reduced electrochemically on a 0.05 mole scale to the corresponding aldehydes and alcohols, depending on conditions, in 50–97% yield. Facile, high-yield reduction of epoxides to alcohols has been reported to be effected without rearrangment by lithium in ethylenediamine. Lithium in methylamine was reported to reduce carboxylic acids to aldehydes or amines, depending on workup, in 50–70% yield.