Alkoxide ions as nucleophiles

While quantitative measurements of pseudobase formation in aqueous alcoholic solutions may be used as indications of the relative susceptibilities to nucleophilic attack for closely related cations,9,53,75,218 such data are not directly comparable with equilibrium and rate data for pseudobase formation in either water or the pure alcohol (or even with data in aqueous alcoholic solutions of other compositions). Several workers218,257,261,262 have reported rate constants for hydroxide ion attack on heterocyclic cations in aqueous alcoholic solutions without any apparent attempt to consider the complications that arise in such media as a result of the competition between hydroxide and alkoxide ions as nucleophiles. The only attempt to measure the relative reactivities of hydroxide and alkoxide ions toward a heterocyclic cation appears to be the work of Gravitz and Jencks306 for the IV,0-trimethylenephthalimidium cation (158). In this study, product analysis indicated the relative proportions of hydroxide and alkoxide adduct... [Pg.64]

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