The reactivity of oxygen nucleophiles with aryl radicals in the S(RN)1 mechanism

Article abstract of DOI:10.1016/S0040-4039(00)74201-8

The photostimulated reaction of 2-naphthoxide ions 1 with o-dihalobenzenes in liquid ammonia gives the halosubstituted product 4 and the cyclized substituted product 5. This is the first report about the coupling of an aromatic σ radical with an oxygen functionality in the chain propagation cycle of the S(RN)1 mechanism.