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The Radical-anions and Dianions of Aromatic Hydrocarbons in Metallation Reactions

The review gives a general account of the literature data on the behaviour of the radical-anions and dianions of aromatic hydrocarbons in reactions involving the metallation of aliphatic–aromatic compounds and discusses the mechanisms of these reactions, the role of the counterion, the degree of its solvation, and the type of ionic association complexes in solutions of the reactants being emphasised. Since the carbanions of dihydro-derivatives of aromatic hydrocarbons are formed in the course of the reactions, data are presented also on their involvement in the metallation processes. The relative protophilic properties of the three types of metallating agents, established experimentally and determined from the localisation energies of their protonation reactions calculated by the Pariser–Parr–Pople method, are compared. The bibliography includes 120 references.