Axially chiral 2-arylimino-3-aryl-thiazolidine-4-one derivatives: Enantiomeric separation and determination of racemization barriers by chiral HPLC
JOURNAL OF ORGANIC CHEMISTRY, cilt.72, sa.7, ss.2494-2500, 2007 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 72 Sayı: 7
- Basım Tarihi: 2007
- Doi Numarası: 10.1021/jo0625554
- Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
- Sayfa Sayıları: ss.2494-2500
- İstanbul Üniversitesi-Cerrahpaşa Adresli: Hayır
Özet
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.