Peroxy Esters. 8. Base-Catalyzed Rearrangement of Peroxy Esters: Formation of Alkoxyacetic Acid Derivatives

Article abstract of DOI:10.1021/jo00169a016

p-Peroxyquinol esters derived from base-catalyzed oxygenation of 4-alkyl-2,6-tert-butylphenols followed by Schotten-Baumann acylation undergo a novel base-catalyzed rearrangement with t-BuOK in N,N-dimethylformamide to give p-quinoxyacetic acid derivatives in excellent yield.The same base-catalyzed rearrangement was also observed with tert-butyl peroxy esters.The base-catalyzed reaction of peroxy esters depended strongly on the nature of the acyl group in the esters and the base used and is suggested to involve homolysis of the peroxy bond.