Determination of the absolute configuration of three as-hydrindacene compounds by vibrational circular dichroism

T Kuppens; K Vandyck; J Van der Eycken; W Herrebout; B J van der Veken; P Bultinck

doi:10.1021/jo050666h

Determination of the absolute configuration of three as-hydrindacene compounds by vibrational circular dichroism

J Org Chem. 2005 Nov 11;70(23):9103-14. doi: 10.1021/jo050666h.

Authors

T Kuppens¹, K Vandyck, J Van der Eycken, W Herrebout, B J van der Veken, P Bultinck

Affiliation

¹ Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, B-9000 Gent, Belgium.

PMID: 16268579
DOI: 10.1021/jo050666h

Abstract

[Structure: see text]. The absolute configurations of three compounds with a rigid 1,8-disubstituted as-hydrindacene skeleton have been determined using vibrational circular dichroism spectroscopy and quantum chemical calculations. Experimental spectra were compared to B3LYP/6-31G and B3LYP/cc-pVTZ level predicted spectra. Based on the agreement between the predicted and experimental spectra, the stereochemistry could be assigned with high confidence. The results were found to be in agreement with ECD determinations and/or predictions based on the applied asymmetric methods in the synthetic route.