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Updated: Jul 2, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
The three-dimensional structural characterization of hexachlorocyclopentenyl-dibromocyclooctane (HCDBCO)
N Riddell1, G Arsenault, A Lough
1Wellington Laboratories, Research Division, Guelph, Ontario, Canada N1G 3M5.
Abstract:
The 1H NMR spectrum and the crystal structure of HCDBCO [(1R,2R,5R,6R,9S,10S)-5,6-dibromo-1,10,11,12,13,13-hexachlorotricyclo[8,2,1,0(2,9)]-tridec-11-ene)] are reported. The measured dihedral angles from the X-ray structure correlate very well with those calculated from the proton-proton coupling constants indicating that the conformations in solution and in the solid state are probably very similar. Attempts at calculating the 3D model structure of HCDBCO only produced a very poor match between the measured dihedral angles between vicinal protons and the observed proton-proton coupling constants from the 1H NMR spectrum. GC/MS analysis with an injector temperature of 250 degrees C produced minor amounts of debrominated HCDBCO. Reducing the temperature to 200 degrees C eliminated this problem.
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