Determination of barriers to rotation of axially chiral 5-methyl-2-(o-aryl)imino-3-(o-aryl)thiazolidine-4-ones
CHIRALITY, cilt.24, sa.6, ss.493-498, 2012 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 24 Sayı: 6
- Basım Tarihi: 2012
- Doi Numarası: 10.1002/chir.22007
- Dergi Adı: CHIRALITY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.493-498
- Anahtar Kelimeler: axial chirality, hindered rotation, barrier to rotation, enantioselective HPLC, separation of diastereomers, thermal interconversion, ATROPISOMERIC PHOSPHINE-LIGANDS, ASYMMETRIC ALLYLIC ALKYLATION, ENANTIOMERIC SEPARATION, RACEMIZATION BARRIERS, DERIVATIVES, RESOLUTION, CATALYSIS, SERIES
- İstanbul Üniversitesi-Cerrahpaşa Adresli: Hayır
Özet
Thermally interconvertible axially chiral 5-methyl-2-(o-aryl)imino-3-(o-aryl)-thiazolidine-4-ones have been synthesized diastereoselectively, and conformations of the major and minor enantiomeric pairs have been determined by 1H nuclear magnetic resonance. Chromatographic resolutions of each compound have been performed by enantioselective high-performance liquid chromatography, and the barriers to rotation about the N3-Caryl bond have been determined by following the thermal interconversion process of the major to minor isomers until equilibrium. The rotational barriers range from 96.2 to 115.2?kJ/mol, depending on the size of ortho substituent on N3-aryl ring. Chirality 24:493498, 2012. (c) 2012 Wiley Periodicals, Inc.