Abstract

The nucleoside, 5′-( t-butyl-dimethylsilyl)-2′,3′-O-isopropylidene isoG 1, catalyzes the S N2 reactions of alkali and ammonium iodides with dodecyl mesylate 2 under both liquid-liquid and solid-liquid phase transfer conditions. IsoG 1 self-associates to give a complex that extracts the salts into CDCl 3 solution. Sodium iodide, in the presence of isoG 1, reacts faster with 2 than the other iodides under solid-liquid conditions. This reactivity difference is attributed to the open-faced structure of the ionophore-M + complex under solid-liquid conditions.

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