In our continuing systematic studies concerning the synthesis, drolytic, decomposition.
surface properties, and hydrolysis of chemodegradable, diastereo-
In our previous papers we reported on the relation between merically pure surface active 2,5-disubstituted 1,3-dioxane derivasurface activity and configuration at the C-5 atom of a polar tives, two new groups of anionic surfactants, sodium cis-and transsubstituent directly joined to the 1,3-dioxane ring, i.e., a (2-n-undecyl-1,3-dioxan-5-yl)methyl sulfates and sodium cis-and hydroxyl group in cis-and trans-2-n-alkyl-5-hydroxy-1,3trans-3-[(2-n -undecyl-1,3-dioxan-5-yl)oxy]propanesulfonates, dioxanes, which do not form micelles in aqueous solution were synthesized and investigated. Surface properties of these sur-(9, 10), or a sulfate group in micelle-forming sodium cisfactants, i.e., surface excess concentration, G, surface area demand and (trans-2-n-alkyl-1,3-dioxan-5-yl) sulfates (11). In the per molecule, A, effectiveness of surface tension reduction, P, critical micelle concentration, CMC, and standard free energies of present paper we show the results of surface activity and adsorption, DG 0 ads , and of micellization, DG 0 mic , were determined. hydrolysis investigations of diastereomerically pure repre-It was shown that the trans-isomers, in which the configuration sentatives of two new groups of micelle-forming surfactants:
of the polar group is equatorial, are more surface active than the sodium cis-and trans-(2-n-undecyl-1,3-dioxan-5-yl)methyl cis-isomers with axial configuration of the polar group at the C-5 sulfates (cis-8 and trans-8 in Fig. ) and sodium cis-and carbon atom of the 1,3-dioxane ring. The surfactants under study trans-3-[(2-n-undecyl-1,3-dioxan-5-yl)oxy]propanesulfonates undergo easy hydrolysis reaction in DCl/D 2 O solution with cleav-(cis-10 and trans-10 in Fig. 1), which contain a methylene age of the 1,3-dioxane ring to nonsurface active intermediates. The or an oxytrimethylene group as a spacer linking a sulfate or trans-isomers are hydrolyzed faster than cis-isomers. ᭧ 1997 Academic sulfonate group to the C-5 atom of the 1,3-dioxane ring, Press respectively.