Abstract
A very pronounced effect of solvent and cation has been found in the investigated reaction, indicating that ion-pairing is indispensable in the title product formation. A simple rationale has been provided assuming self assembly of the complementary reactants driven by hydrogen bonding and ion-pairing interactions. Concomitantly, halogen exchange between the reaction partners has been demonstrated to be a concurrent pathway, resulting from the nucleophilic 2-naphthoxide attack at the bromine terminus of the Cα–Br bond in the participating 1-bromo-2-naphthol.
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