Axially chiral 2-arylimino-3-aryl-thiazolidine-4-one derivatives: enantiomeric separation and determination of racemization barriers by chiral HPLC.
Axially chiral 2-arylimino-3-aryl-thiazolidine-4-ones have been synthesized as racemic mixtures, and each mixture with the exception of 2-(o-chlorophenyl)imino-3-(o-chlorophenyl)-thiazolidine-4-one has been converted to the corresponding 5-benzylidene-2-arylimino-3-aryl-thiazolidine-4-one racemates by reaction with benzaldehyde. The thermally interconvertible enantiomers of each compound have been obtained by enantioselective HPLC separation on columns Chiralpak AD-H and Chiralcel OD-H, and the barriers to racemization have been found to be 98.1-114.1 kJ/mol. The barriers determined were compared to those of structurally related compounds to provide evidence for the stereochemistry of the aryl imino bond.
Erol
Sule
S
Chemistry Department, Bogaziçi University, Bebek 34342, Istanbul, Turkey.
Dogan
Ilknur
I
D002851:Chromatography, High Pressure Liquid; D007097:Imines / Q000737:chemistry* / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012997:Solvents; D013237:Stereoisomerism; D053778:Thiazolidines / Q000737:chemistry* / Q000302:isolation & purification*
D007097:Imines; D012997:Solvents; D053778:Thiazolidines