Reactivity of co-micellar systems based on dimeric functionalized tetraalkylammonium surfactant in phosphoryl and sulfonyl group transfer processes

Abstract

The reactivity of co-micellar systems based on dimeric functionalized tetraalkylammonium surfactant in phosphoryl and sulfonyl group transfer processes is lower than the reactivity of systems based on analogous imidazolium surfactant. The observed difference in the kinetics of acyl group transfer promoted by dimeric surfactants differing by the nature of the cationic center is likely to be general, and it results from both different nucleophilicities of their oximate fragments and different modes of solubilization of hydrophobic substrates. The most probable reasons for the latter are differences in intramolecular Coulomb interactions and packing of surfactant molecules in co-micelles.