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Axially chiral 2-arylimino-3-aryl-thiazolidine-4-ones have been synthesized as racemic mixtures, andeach mixture with the exception of 2-(
o-chlorophenyl)imino-3-(
o-chlorophenyl)-thiazolidine-4-one hasbeen converted to the corresponding 5-benzylidene-2-arylimino-3-aryl-thiazolidine-4-one racemates byreaction with benzaldehyde. The thermally interconvertible enantiomers of each compound have beenobtained by enantioselective HPLC separation on columns Chiralpak AD-H and Chiralcel OD-H, andthe barriers to racemization have been found to be 98.1-114.1 kJ/mol. The barriers determined werecompared to those of structurally related compounds to provide evidence for the stereochemistry of thearyl imino bond.
