Self-assembled ionophores as phase transfer catalysts

The nucleoside, 5'-(t-butyl-dimethylsilyl)-2',3'-O-isopropylidene isoG 1, catalyzes the S(N)2 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 CDCl3 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. (C) 1999 Elsevier Science Ltd. All rights reserved.