Reactions of Carboxylic Acid Derivatives with Superoxide
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.
Forrester, Alexander R.,Purushotham, Vemeshetti
p. 945 - 951
(2007/10/02)
Mechanism of Hydrolysis of Esters by Superoxide
Experimental evidence is presented indicating that hydrolysis of an ester by superoxide in an aprotic solvent does not proceed via the corresponding acyl peroxide, although the peroxycarboxylate anion is involved.