Abstract
Abstract The alkylation of sodium 2-naphtholate, in the presence of benzo-18-crown-6 or 4,7,13,16,21,24-hexaoxabicyclo[8.8.8]hexacosane is found to give high ratios of O/O+C alkylation when conducted in THF, in benzene, and in water. The striking increase in the product ratio is attributed to a specific complexation of the macrocyclic polyethers, which facilitate the dissociation of the ion-pair aggregate of the sodio-derivative which exists in benzene or THF. The polyethers may act as phase-transfer catalysts when the reaction is run in water. In support of this conclusion, the reaction in DMF or acetonitrile, in which the dissociation of sodium 2-naphtholate takes place, fails to show any effect of the macrocyclic polyethers on the product ratio.
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