Collect. Czech. Chem. Commun.
2000, 65, 477-489
https://doi.org/10.1135/cccc20000477
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.
Abstract
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.
