Journal article

Publication year: 2002

Pages: 13348-13349

Journal: Journal of the American Chemical Society

Volume number: 124

Issue number: 45

ISSN: 0002-7863

DOI Link: https://doi.org/10.1021/ja0274195

Publisher: American Chemical Society

Abstract: 

Pseudotetrahedral, conformationally as well as configurationally stable 1-bromo-3-chloro-5-fluoro- (4) and 1-bromo-3-chloro-5-fluoro-7-iodoadamantane (5)
(and some related compounds) were prepared by our recently devised
phase-transfer catalytic halogenation protocol; the optical antipodes of
4 were separated by HPLC on chiral phase in ee > 99%, and the
absolute configurations were assigned by matching observed and computed
circular dichroism spectra. Structure 5 is the first chiral
aliphatic hydrocarbon containing all stable (nonradioactive) halogens;
its structure was proven by NMR spectroscopy and by X-ray crystal data.
We emphasize that the combination of experiment and theory is very
powerful in assigning absolute configurations even for molecules without
typical chromophors, with small values for the optical rotation, and
without an atom at the stereogenic center.

Harvard Citation style: Schreiner, P., Fokin, A., Lauenstein, O., Okamoto, Y., Wakita, T., Rinderspacher, C., et al. (2002) Pseudotetrahedral polyhaloadamantanes as chirality probes: Synthesis, separation, and absolute configuration, Journal of the American Chemical Society, 124(45), pp. 13348-13349. https://doi.org/10.1021/ja0274195

APA Citation style: Schreiner, P., Fokin, A., Lauenstein, O., Okamoto, Y., Wakita, T., Rinderspacher, C., Robinson, G., Vohs, J., & Campana, C. (2002). Pseudotetrahedral polyhaloadamantanes as chirality probes: Synthesis, separation, and absolute configuration. Journal of the American Chemical Society. 124(45), 13348-13349. https://doi.org/10.1021/ja0274195