Enantiomers of sterically hindered n-aryl-4-pyridones: Chromatographic enrichment and thermal interconversion |
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Authors: | M. Mintas Z. Orhanović K. Jakopčić H. Koller G. Stühler A. Mannschreck |
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Affiliation: | Department of Organic Chemistry, Faculty of Technology, University of Zagreb, Maruli?ev trg 20, Y-41000 ZagrebYugoslavia;Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, D-8400 RegensburgFrg |
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Abstract: | N-Aryl-4-pyridones 1–6 were synthesized by condensation of the corresponding 4-pyrone with anilines. The enrichment of the enantiomers was achieved by liquid chromatography on triacctylcellulose, enantiomeric purities of(+)-1 and (+ )-2 being measured by 1H-NMR in the presence of an optically active auxiliary. Barriers to partial rotation about the C-N bond in 1-4 were determined and compared with corresponding biphenyls. |
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