SYNTHESIS OF 1-HYDROXYETHYL-2-DIMETHYL ALKYLAMMONIUM SURFACTANTS AND THEIR PROPERTIES IN AQUEOUS SOLUTION

A general synthetic method for the synthesis of a new class of chiral surfactants with reactive OH groups was investigated. The surfactarits were made by quaternizing the corresponding tertiary amine, in isopropyl alcohol. These surfactants with -OH groups may form tightly-packed non-spherical micelles in the presence of WaOH or alkylamine and these .micelles, just like enzyme catalysts, may serve as stereoselective templates. In order to evaluate this stereospecificity, a kinetic study of the reactivity of several chi~al reactants in the presence of these micelles, was initiated. The first-order rate constant K for 4- nitrostyrene formation from p-nitrophenethyl trimethylammonium iodide in 0.1 M NaOH at 39°C, increased as a function of surfactant concentration Cs in a manner suggesting micellar catalysis. The data show that N-methyl Ndodecyl 3-hydroxy-piperidinium bromide (DPBr) is a better catalyst than N,N-dimethyl-N-[2-hydroxyethyTI N-hexadecylammonium bromide (CTOH) in the E2 elimination, probably because it is more hydrophobic. This high activity suggests that chiral surfactants may induce chirality