Partially fluorinated naphthalene derivatives from 1,4-dilithio-1,3-dienes and C6F6

Multi-substituted partially fluorinated aromatic compounds, such as naphthalene derivatives could be readily prepared by the reaction of 1,4-dilithio-1,3-dienes with hexafluorobenzene via double nucleophilic substitution. When these dilithium reagents were treated with hexachlorobenzene, chloropentafluorobenzene or bromopentafluorobenzene, chlorine–lithium or bromine–lithium exchange reactions, instead of nucleophilic substitution, took place.