Collect. Czech. Chem. Commun. 2000, 65, 477-489

Circular Dichroism and Conformational Analysis of Diastereomeric Bicamphors

Stefan E. Boiadjiev and David A. Lightner*

Chemistry Department, University of Nevada, Reno, Nevada 89557, U.S.A.


Stereospecific syntheses afforded endo,endo- (1) and exo,exo- (2) bicamphors, while the third possible diastereomeric exo,endo-bicamphor (3) originated from nonselective camphor radical dimerization. The stereochemistry of bicamphor linkage was confirmed by 1H NMR analysis. Chiroptical and ultraviolet spectral data are presented for the three diastereomers 1-3 to show interchromophoric interaction. Conformational analysis to evaluate the relative orientation of each pair of carbonyl chromophores was accomplished by 1H NMR spectroscopy and molecular mechanics calculations.

Keywords: Camphor dimers; Molecular mechanics; Stereochemistry; Conformation analysis; CD spectroscopy; UV spectroscopy; NMR spectroscopy, 1H and 13C; Terpenoids.

References: 39 live references.