Further studies on the stereochemistry of sparteine, its isomers and derivatives: Part XXII. 13C NMR analysis of sparteine derivatives substituted in external rings — monosalts

Add time:08/21/2019    Source:sciencedirect.com

The 13C NMR spectra of six sparteine derivatives were analysed. In four of them, the substituent phenyl, methyl or cyano was in the external A ring of the molecule at C(2), while in the other two, the substituent was attached to C(15) in ring D. The analysis was based on a comparison of the spectra of the studied monocations with the spectra of the sparteine monocation taken under the same conditions, including the off-resonance spectra. This work was aimed at determining the character of the changes in the chemical shift (substituent and protonation effects), to provide a greater insight into the configurational—conformational changes of the sparteine skeleton in CD3CN solution. All the analysed derivatives adopt the all-chair trans-A/B: cis:-C/D bis-quinolizidine skeleton.

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