Electrosynthesis in systems of two immiscible liquids and a phase transfer catalyst. V. The anodic chlorination of naphthalene

The anodic chlorination of naphthalene in a water/methylene chloride emulsion and using tetrabutylammonium ion as the phase transfer catalyst is demonstrated; in conditions where the aqueous phase is saturated NaCl, the organic yield of 1-chloronaphthalene is 56% and the current yield is 33% after the passage of 2.33 F mol^–1 of naphthalene. It is shown, however, that when the aqueous phase also contains zinc chloride so that the species transferred is [(C₄H₉)₄N⁺]₂ZnCl₄^––, the yields can be increased to 92% and 49% respectively. The mechanism of these chlorinations is discussed.