| Abstract: | Solvent effects on the intrinsic activity of, the ion-exchange rate of, and the overall activity of polymer-supported phosphonium salts under tri-phase conditions were studied. The intrinsic activity of the catalysts as well as of soluble phosphonium salts was dependent only slightly on organic solvents. The exchange rate of the chloride ion in the catalysts against the acetate ion dependent on the solvents when the degree of ring substitution was ≤ 16%. With the ca. 30% ring-substituted catalysts the rate increased and hardly depended on the solvents. The overall reactivity of the catalysts for the reaction of organic halides with NaCN was a function of substrate structure and organic solvents. For alkyl halides such as bromooctane the catalysts were more reactive in good solvents such as toluene or chlorobenzene than in poor solvents such as octane. For arylalkyl halides such as benzyl chloride the catalysts exhibited the opposite effect. In poor solvents the arylalkyl halides are absorbed preferentially into the catalysts. |
