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Twisting the ethano-Tröger's base: the bisamide.

Raul Pereira1, Lukas Pfeifer2, Jean Fournier3

  • 1Department of Chemistry, University of Oxford, 12 Mansfield Road, OX1 3TA Oxford, UK. veronique.gouverneur@chem.ox.ac.uk and Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Zürich, Vladimir-Prelog-Weg-2, 8093 Zürich, Switzerland. cvengros@inorg.chem.ethz.ch.

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Researchers created twisted bisamides by selectively oxygenating ethano-Tröger

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Stereochemistry

Background:

  • Amide groups are typically planar, influencing molecular properties and reactivity.
  • Incorporating amides into bicyclic systems can induce significant distortions from planarity.
  • These distortions lead to unique physical and chemical behaviors compared to classical amides.

Purpose of the Study:

  • To develop a concise method for synthesizing non-planar bisamide compounds.
  • To explore the synthesis of ethano-Tröger's base derivatives with ortho-nitrogen substituents.
  • To investigate the impact of distorted amide geometry on molecular properties.

Main Methods:

  • Utilized potassium permanganate for selective α-oxygenation.
  • Targeted the benzylic position of ethano-Tröger's base derivatives.
  • Developed a protocol for synthesizing substituted ethano-Tröger's base derivatives.

Main Results:

  • Successfully synthesized a new class of twisted bisamides.
  • Achieved selective α-oxygenation at the benzylic position.
  • Reported the first synthesis of ethano-Tröger's base derivatives with ortho-nitrogen substituents.

Conclusions:

  • The developed protocol provides access to novel twisted bisamide structures.
  • Distorted amide geometries in bicyclic systems offer unique chemical reactivity.
  • This work expands the synthetic accessibility of complex nitrogen-containing heterocycles.