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Wagner‐Meerwein rearrangement of a [3.3.3]‐ to a [4.3.3]propellane: deuterium tracer and conformational analysis
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AbstractFormation of (−)‐[4.3.3]propellane 4 from (−)‐14‐hydroxymodhephene (2) proceeds through a Wagner‐Meerwein rearrangement via C3C4 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.
Title: Wagner‐Meerwein rearrangement of a [3.3.3]‐ to a [4.3.3]propellane: deuterium tracer and conformational analysis
Description:
AbstractFormation of (−)‐[4.
3.
3]propellane 4 from (−)‐14‐hydroxymodhephene (2) proceeds through a Wagner‐Meerwein rearrangement via C3C4 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.
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