6.5.1 The S_RN1 Reaction

Unactivated aryl halides proceed nucleophilic substitution with typically enolates, amide ion and thiol anion via a chain reaction involving anion radicals in that the initiation step is an electron transfer. The first two steps are similar to those in S_N1 reaction which led to the designation S_RNI (R for radical).

The initiation of the reaction is generally either by solvated electron (sodium in liquid ammonia) or with photochemical excitation in that the nucleophile is the electron donar. For examples,