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Anwendung der NMR-Spektroskopie chiraler Assoziate 15: Flüssigkeits-Chromatographie an Triacetylcellulose 10: The enantiomers of N,N-dimethylthiobenzamides: Chromatographic behaviour and rotational barriers

Eiglsperger, A. ; Kastner, F. ; Mannschreck, Albrecht



Abstract

N,N-Dimethylthiobenzamides bearing hydrogen atoms in both orthopositions were shown by 1H NMR in the presence of an optically active alcohol to have non-coplanar π-systems. The barrier to rotation about the C(sp2-C(sp2) bond amounts to 43 ± 2 kJ/mol. Liquid chromatography on triacetylcellulose served for the enrichment of enantiomers of 2-substituted thiobenzamides. In several cases considerable ...

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