Wagner-Meerwein rearrangement of a [3.3.3]- to a [4.3.3]propellane: deuterium tracer and conformational analysis

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 la...

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Bibliographic Details
Published in:Magnetic resonance in chemistry 2007-04, Vol.45 (4), p.346-350
Main Authors: Reyes-Trejo, Benito, Morales-Ríos, Martha S., Joseph-Nathan, Pedro
Format: Article
Language:English
Subjects:
conformational analysis
deuterium labeling
isotope effects
molecular modeling
propellanes
Wagner-Meerwein rearrangement
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Summary: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 © 2007 John Wiley & Sons, Ltd.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.1978