Reactivity–selectivity relationships. Part 7. Solvent effects on the selectivity of adamantyl derivatives in aqueous ethanol

Abstract

The influence of solvent composition on the selectivity (k_W/k_E) of adamantyl derivatives toward ethanol and water is investigated. Variations in the proportions of ethanol and water in binary mixtures were found to have little effect on substrate selectivity. Addition of acetone, however, to a 60% aqueous ethanol solution is found to increse substrate selectivity. These results are interpreted as evidence for a change in the relative nucleophilicity of ethanol and water in different solvent compositions. The implication of these results for octyl, benzyl, and diphenylmethyl systems is discussed.