Abstract
The thin-layer chromatographic (TLC) retentions on silica of twenty diastereoisomeric compounds of the type ROOCCH CHCOOR were studied as the group R varied from methyl to isopentyl and cyclohexyl. Twenty-one mobile phases were used having strengths, ϵ, in the range 0.215–0.316 and a wide variation of solvent selectivity effects. Owing to a site chelation via the two ester groups, the ( Z)-maleate was always more strongly retained than the corresponding ( E)-fumarate. An increase in both steric effects and solvent selectivity effects did not change the relative retention but affected the retention of the diastereoisomers. TLC is suitable for assigning the configurations of other compounds from the group studied.
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