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Updated: Feb 21, 2026
09:08
A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
Published on: February 27, 2017
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Synthesis of trinorbornane
Lorenzo Delarue Bizzini1, Thomas Müntener, Daniel Häussinger
1Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland. marcel.mayor@unibas.ch.
Chemical Communications (Cambridge, England)
|October 5, 2017
Summary
Researchers synthesized and characterized a novel chiral C11 tetracyclo[5.2.2.01,6.04,9]undecane skeleton, also known as "trinorbornane." This unique rigid structure, previously only theoretical, has now been realized in the lab.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Stereochemistry
Background:
- The exploration of novel carbon skeletons is crucial for advancing molecular complexity.
- Rigid polycyclic structures offer unique properties for materials science and drug discovery.
- The tetracyclo[5.2.2.01,6.04,9]undecane framework was computationally predicted but synthetically elusive.
Purpose of the Study:
- To report the first synthesis and characterization of the chiral C11 tetracyclo[5.2.2.01,6.04,9]undecane skeleton.
- To provide a real-world counterpart to a theoretically predicted molecular structure.
- To establish a new class of rigid polycyclic compounds.
Main Methods:
- Multi-step organic synthesis.
- Characterization using spectroscopic techniques (e.g., NMR, Mass Spectrometry).
- Analysis of stereochemistry and structural rigidity.
Main Results:
- Successful synthesis of the unreported chiral C11 tetracyclo[5.2.2.01,6.04,9]undecane ("trinorbornane").
- Achieved in 7% overall yield over 9 synthetic steps.
- Confirmed the existence of this rigid structural type, previously only found in computational databases.
Conclusions:
- The synthesis validates the existence of the "trinorbornane" skeleton in reality.
- This work expands the repertoire of known chiral polycyclic hydrocarbons.
- Opens avenues for exploring the properties and applications of this novel rigid framework.
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