1095347-57-1Relevant articles and documents
NMR elucidation of a novel (S)-pentacyclo-undecane bis-(4-phenyloxazoline) ligand and related derivatives
Boyle, Grant A.,Govender, Thavendran,Kruger, Hendrik G.,Maguire, Glenn E. M.,Naicker, Tricia
, p. 1089 - 1095 (2008)
The NMR elucidation of a novel ligand (S)-pentacyclo-undecane bis-(4-phenyloxazoline) and related pentacyclo-undecane (PCU) derivatives is reported. Two-dimensional NMR proved to be a powerful technique in overcoming the difficulties associated with the elucidation of these compounds when only one-dimensional NMR data is utilized. A chiral substituent was introduced to both 'arms' of the PCU skeleton to produce derivatives 1-3. These derivatives display C1 symmetry with all thecage atoms being nonequivalent. Owing to overlapping of peaks in the 1H spectra, identification of these diastereomeric protons was very difficult. The 13C spectra gave rise to clear splitting of the nonequivalent carbons. This is unusual compared to similar PCU derivatives with chiral substituents as splitting of all the diastereomeric cage carbons has not yet been reported. Nuclear Overhauser enhancement spectroscopy (NOESY) correlations of derivatives 1-3 confirm the different conformations of the molecule in which the side 'arms' occupy different orientations with respect to cage moiety. Copyright