Journal
MAGNETIC RESONANCE IN CHEMISTRY
Volume 45, Issue 4, Pages 346-350Publisher
WILEY
DOI: 10.1002/mrc.1978
Keywords
propellanes; deuterium labeling; Wagner-Meerwein rearrangement; isotope effects; conformational analysis; molecular modeling
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Formation of (-)-[4.3.3]propellane 4 from (-)-14-hydroxymodhephene (2) proceeds through a Wagner-Meerwein rearrangement via C3-C4 bond-shift to give a stable intermediate, dimethylcyclohexadienyl cation A, which undergoes deprotonation. Herein, this mechanism was investigated by using a deuterium labeled substrate at the C-14 methylene group of (-)-2, which was incorporated into the C-4 position of (-)-[4.3.3]propellane 4. The stereostructure of (-)-4 was investigated by applying a combination of NMR experimental and theoretical approaches. Copyright (C) 2007 John Wiley & Sons, Ltd.
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