Abstract
The mechanisms of the reactions of superoxide with carboxylic esters, acyl peroxides, and the acyl chlorides of α- and β-bromocarboxylic acids have been investigated. Experimental evidence is presented supporting the view that (a) conversion of an ester into its carboxylic acid does not proceed via the corresponding acyl peroxide; (b) conversion of acyl peroxide into carboxylic acid by superoxide involves either electron transfer to or an SN2 reaction on the peroxidic group; (c)α-bromoacyl chlorides with superoxide give the corresponding aldehyde via a cyclic peroxidic intermediate.
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