Active-alkali metal-promoted reductive cleavage of chlorinated phenols

We investigated the degradation of chlorinated phenols under reductive electron transfer reaction condi- tions. Although Li and Na metal proved useless, activated forms of these metals, either their soluble naphthalene radical anions or 1,2-diarylethane dianions, promoted the degradation of the starting materials to various extents. Additionally, efficient dehalogenation of the sodium salts of several mono-, di-, and tri-chlorophenols was obtained by their reduction with an excess of Na metal and a cata- lytic amount of naphthalene.