ELECTROCHEMICAL OXIDATION OF ENAMINES IN THE PRESENCE OF ORGANIC-ANIONS

Anodic oxidations of enamines were examined in the presence of organic anions derived from methyl acetoacetate, acetylacetone, and dimethyl malonate. Enamines are very readily oxidized at a platinum anode and are substituted by the anionic substrates. The produced enamine intermediates are hydrolyzed with dilute hydrochloric acid to the corresponding α-substituted ketones. By treatment with more concentrated hydrochloric acid, some of them are converted to furan derivatives involving an intramolecular condensation. © 1979, American Chemical Society. All rights reserved.