Abstract
Chiral title compounds have been resolved by medium pressure liquid chromatography (MPLC) on triacetylcellulose in ethanol. Whereas a quantitative separation was achieved for16 and20, a recycling technique had to be applied to1,4,6,10 and15 leading to a 100% e.e. for1,6 and15 and to ca. 60% e.e. for4 and10.
An unambiguous assignment of the chirality (+)-(R) a -(S) m for tricarbonylchromium-6,6′-dimethyl-diphenicacid dimethylester (4) was deduced both from the photochemical decomplexation to (-)-5 with the known chirality (R) a (whose e.e. was determined by MPLC on triacetylcellulose) and by comparison of the1H-n.m.r. spectra of4 and5 thereby proving the structure 4 for the former.
Other chiralities both for mono and bis(tricarbonylchromium)biphenyl complexes were established by chemical correlations and comparison of the CD spectra with those of key compounds.
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Herrn Prof. Dr.H. Tuppy mit besten Wünschen zum 60. Geburtstag gewidmet.
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Eyer, M., Schlögl, K. & Widhalm, M. Biphenyl-tricarbonylchrom-komplexe, 9. Mitt.: Synthesen, chromatographische Enantiomerentrennung, Circulardichroismus und Chiralität von mono- und bis-(Tricarbonylchrom)-Komplexen di- und tetrasubstituierter sowie überbrückter Biphenyle. Monatsh Chem 115, 1429–1442 (1984). https://doi.org/10.1007/BF00816342
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DOI: https://doi.org/10.1007/BF00816342