Synthesis of Novel Polyhydroxyl Surfactants. Influence of the Relative Stereochemistry on Surfactant Properties

This thesis deals with the synthesis and characterization of novel polyhydroxyl surfactants. The first part describes the synthesis of a number of stereoisomers of a polyhydroxyl surfactant, and the second part concerns surface chemical characterization. A stereodivergent route for preparation of the hydrophilic head group was developed, featuring consecutive stereoselective dihydroxylations of a diene. This afforded in total four different polyhydroxyl head groups. These surfactant head groups were natural and unnatural sugar analogues, and were used for the coupling with two different hydrophobic tail groups. Three of these surfactants were used to investigate the chiral discrimination in Langmuir monolayers at an air-water interface. The isotherms showed a remarkable difference in compressibility between surfactants of diastereomeric relationship and also a pronounced chiral discrimination between racemic and enantiomerically pure surfactants favoring heterochiral discrimination. Licentiate Thesis Kungliga Tekniska Högskolan Department of Chemistry Organic Chemistry © Kristina Neimert-Andersson 2003 ISBN 91-7283-644-X Ekonomi-Print, Stockholm