Barriers to Stereoinversion of N-Aryl-1,3,2-benzodithiazole 1-Oxides Studied by Dynamic Enantioselective Liquid Chromatography
Free energies of activation for the enantiomerization of a series of racemic N-aryl-1,3,2-benzodithiazole 1-oxides have been determined by dynamic high-performance liquid chromatography (DHPLC) on a chiral stationary phase. From a comparison of experimental and computer-simulated chromatograms, the...
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| Veröffentlicht in: | Journal of organic chemistry Jg. 64; H. 5; S. 1483 |
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| Hauptverfasser: | , |
| Format: | Journal Article |
| Sprache: | Englisch |
| Veröffentlicht: |
United States
05.03.1999
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| ISSN: | 1520-6904, 1520-6904 |
| Online-Zugang: | Weitere Angaben |
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| Zusammenfassung: | Free energies of activation for the enantiomerization of a series of racemic N-aryl-1,3,2-benzodithiazole 1-oxides have been determined by dynamic high-performance liquid chromatography (DHPLC) on a chiral stationary phase. From a comparison of experimental and computer-simulated chromatograms, the barriers to stereoinversion at sulfur were found to be around 80 kJ/mol and relatively insensitive to effects from substituents in the N-aryl group. Throughout the series the (+)-forms (436 nm) were found to be of (S)-configuration. |
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| Bibliographie: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 1520-6904 1520-6904 |
| DOI: | 10.1021/jo981885o |