SELECTIVITY IN RAPID INTERFACIAL REACTIONS OF HYDROPHOBIC SUBSTRATES BOUND TO POLYMER-SUPPORTED ORGANIC-PHASE

Rapid heterogeneous reactions were studied between an aqueous nucleophile and alkyl bromides and alkyl arenesulfonates bound to the surface of alkylsilylated silica gel or alkylated polymer gels. Without agitation in the reaction system, typical nucleophilic substitution reactions proceeded at the phase boundary much faster than conventional liquid-liquid two-phase reactions. This is due to the large surface area of the support and the extremely thin organic phase which held the substrate molecule at the interface. While the silica-supported organic phase resulted in selective reaction of alkyl arenesulfonates compared with alkyl bromides, the polymer supported organic phase showed the opposite tendency. The differences in the interfacial reactivity were accounted for by the mode of binding of the substrate to the supported organic phase.