POLYMERIC COSOLVENTS - COOPERATION OF POLYMER BOUND QUATERNARY AMMONIUM GROUPS AND N,N-DIALKYLAMIDE GROUPS IN ACTIVATION OF THE PHENOXIDE ANION

By a series of quaternization and amidoalkylation reactions a series of polymers I-IV was prepared, based on microporous poly(styrene-98-co-divinylbenzene-2), (PS-DVB). The polymers contain quaternary ammonium groups (Q) and carboxamide groups (L) imitating polar aprotic solvents, i.e. N,N-dimethylacetamide and N-methyl-2-pyrrolidone. These two types of functional groups L, Q exhibit a cooperative effect in the activation of sodium phenoxide in its reaction with 1-bromooctane. The measure of the cooperative effect depends on the type of isolation of the sites in which the functional groups L and Q are bound to the polymeric matrix. An increase in the specific rate constants by more than an order of magnitude was observed with such low-functionalized polymers IV in which both functional groups L and Q are bound in one binding site and are separated by a short spacer only.