Premium
Bis[oxo/thioxothiazolinyl] Aromatic Compounds ‐ Synthesis and Conformational Assignment
Author(s) -
Hîrtopeanu Anca,
Suteu Cristina,
Uncuta Cornelia,
Mihai Gheorghe,
Roussel Christian
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200003)2000:6<1081::aid-ejoc1081>3.0.co;2-1
Subject(s) - atropisomer , chemistry , antiparallel (mathematics) , diastereomer , cellulose triacetate , microcrystalline cellulose , circular dichroism , chiral column chromatography , aryl , stereochemistry , column chromatography , organic chemistry , high performance liquid chromatography , cellulose , physics , alkyl , quantum mechanics , magnetic field
A series of bis(oxo/thioxothiazolinyl) aromatic atropisomers with two chiral C(aryl)‐N(heterocycle) axes was synthesized. The separation of antiparallel , parallel diastereomers was achieved by chromatography on silica. Conformational assignment for the bis‐thione atropisomers 1a,b ‐ 4a,b and bis‐one atropisomers 9a,b ‐ 12a,b was based on polarimetric results in analytical chiral chromatography on microcrystalline cellulose triacetate. The relationship conformation‐ 1 H NMR chemical shifts, found for the bis‐thiones and bis‐ones was successfully applied for the conformational assignment of thione‐one atropisomers not assigned by chiral liquid chromatography.