Potassium permanganate/carboxylic acid/organic solvent: A powerful substitute for manganese(III) acetate

ORGN 275

Ayhan S. Demir, asdemir@metu.edu.tr and Hamide Findik. Department of Chemistry, Middle East Technical University, Inonu Bulvari, 06531 Ankara, Turkey
The generation of radicals by transition metals is of current interest in organic chemistry. Among them manganese(III) acetate occupied a unique place. A number of novel accesses to different classes of organic compounds are developed by using manganese(III) acetate. One of the important applications is the selective oxidation of enones. As we reported earlier, the oxidation of enones using manganese(III) reagents prepared from manganese(III) acetate in the presence of various carboxylic acids or manganese(II) salts of these carboxylic acids provided a convenient synthesis of a'-acyloxy enones. These oxidation reactions of enones are carried out with potassium permanganate/carboxylic acid in organic solvent and same acyloxy enones are obtained in high yields. After this result potassium permanganate/carboxylic acid system in organic solvent is applied to many other manganese(III) acetate mediated C-C, C-O bond formation reactions and the results showed that this system is a powerful substitute for manganese(III) acetate.