NUCLEOPHILIC COUPLING OF ALKALI 2-NAPHTHOXIDES WITH 1-BROMO-2-NAPHTHOLS - ION-PAIRING AND HALOGEN DANCE IN THE FORMATION OF 1,1'-BINAPHTHALENE-2,2'-DIOLS

A very pronounced effect of solvent and cation has been found in the i nvestigated reaction, indicating that ion-pairing is indispensable in the title product formation. A simple rationale has been provided assu ming self-assembly of the complementary reactants driven by hydrogen b onding and ion-pairing interactions. Concomitantly, halogen exchange b etween the reaction partners has been demonstrated to be a concurrent pathway, resulting from the nucleophilic 2-naphthoxide attack at the b romine terminus of the C-alpha-Br bond in the participating 1-bromo-2- naphthol.