The Dechlorination of Some Highly Chlorinated Naphthalene Derivatives

Article abstract of DOI:10.1016/0040-4020(95)00396-P

The <4+2> cycloadducts formed between tetrachlorobenzyne and a variety of arenes and cyclic 1,3-dienes have been reductively dechlorinated.The products are formally benzyne cycloadducts, many of which are difficult to make by other routes.High yields are obtained when sodium and t-butanol in boiling THF are used for the reduction.THF serves as a solvent but t-butanol not only acts as a proton donor but also appears to initiate the reduction.Tetrachlorobenzyne should be considered as an alternative reagent whenever benzyne itself appears to be required.