H. Quast, M. Seefelder, E.-M. Peters, K. Peters
FULL PAPER
[14]
H. Quast, C. Becker, E.-M. Peters, K. Peters, H. G. von Schne-
(1S)-4,8-Diphenylbarbaralane-2,6-dicarbonitrile [(1S)-1]: According
to the procedure for rac-1,[4] (1S)-13 (0.98 g, 3.0 mmol) was treated
with hexachloroethane (2.16 g, 9.1 mmol) in a vigorously stirrred
mixture consisting of CH2Cl2 (15 mL), aq. tetrabutylammonium
hydroxide (0.7 mL, 40%) and aq. NaOH (8 mL, 50%). Workup as
described, distillation of the solvent in vacuo, and flash chromatog-
raphy of the dark-red, solid residue with PE/EA (8:2) afforded
brick-red needles (0.64 g, 65%), m.p. 224Ϫ225°C. Recrystallisation
from PE/EA (1:1) yielded crystals that were suitable for an X-ray
diffraction analysis.
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X-ray Diffraction Analyses were performed on transparent, colour-
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red [(1S)-1] crystals. The cell parameters were determined on the
basis of 70 reflections. The number of reflections reported in Table
11 were obtained with Mo-Kα radiation and 2 Θmax ϭ 55° [rac-
endo-4, endo-(1R)-9, exo-(1S)-9, (1S)-3, (1S)-1] or Cu-Kα radiation
and 2 Θmax ϭ 110° [(1R)-7] (graphite monochromator, ω scan).
Measurements were carried out with a system Siemens P4. The
programme SHELXTL PLUS[37] was employed. The structure was
solved by direct methods and refined anisotropically by the least-
squares method. The weighting scheme for Rw is 1/σ2. The posi-
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Solutions in tetrahydrofuran of lithium tris(tert-butoxy)alumin-
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and exo-4, and 5 (HPLC).
Deviating from IUPAC rules of nomenclature for sake of con-
sistency, we use the numbering for the bicyclo[3.3.1]nonane
skeleton of the hydroxy ketones 4 also for their derivatives, viz.
the camphanoates endo-7 and the N-(1-phenylethyl)carbamates
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We express our gratitude to Professor A. Mannschreck, Regens-
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