Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry

Four two-chain dicarboxylic acid surfactants linked with a carbonyl group were synthesized and studied. The compounds exist as meso and (±) diastereomers, and they form aggregates, presumably micelles, at concentrations >10⁻⁵ M. Equilibration of the diacids in benzene at 60 °C (p-toluenesulfonic acid catalyst) gives a 50/50 mixture of meso and (±) diastereomers. Equilibration of the diacids in aqueous base with or without added cosurfactants (CTAB, DDAB) gives mixtures favoring the meso diastereomer by as much as 90/10. This perturbation of diastereomeric equilibria is discussed in terms of hydrophobic enforcement of organic stereochemistry. © 1988, American Chemical Society. All rights reserved.

Duke Scholars

Author Andrew T. McPhail Chemistry