ELECTROCHEMICAL AND SPECTROSCOPIC BEHAVIOR OF TRIFLUOROMETHYLACETOPHENONE IN AQUEOUS AND MICELLAR MEDIUM

The electrochemical behavior of 4-trifluoromethylacetophensne (TFMA) h as been studied in aqueous (2 less than or equal to pH less than or eq ual to 10), micellar, and ethanolic solutions using polarographic tech niques. A slow hydration process of the carbonyl group has been observ ed by means of polarography and W-visible spectrophotometry. Besides t he well-known pH dependence of the electroreduction of aromatic ketone s, C-F bond cleavages concomitant to the ketone reduction occur under electrolysis conditions in alkaline medium (pH = 10) at a very negativ e potential (-1.7 V), leading to the formation of 3-methylacetophenone , which is reduced at this potential with formation of the carbinol an d of symmetrical and dissymmetrical pinncols. Finally, the reduction o f TFMA has been performed in the presence of chiral surfactants in ord er to test their ability to induce an asymmetric induction.