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Updated: Jun 11, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
A cope rearrangement-based route to hexahydroazulenes
Curtis A Seizert1, Valentina D Bumbu, Vladimir B Birman
1Department of Chemistry, Washington University, Campus Box 1134, One Brookings Drive, St. Louis, Missouri 63130, USA.
2-exo-Vinyl-7-alkylidenenorbornanes undergo Cope rearrangement to form hexahydroazulene derivatives. This reaction offers a new synthetic route for complex organic molecules.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Norbornane derivatives are versatile synthetic intermediates.
- Fulvene Diels-Alder adducts provide access to complex polycyclic structures.
Purpose of the Study:
- To investigate the Cope rearrangement of 2-exo-Vinyl-7-alkylidenenorbornanes.
- To explore a novel synthetic pathway to hexahydroazulene derivatives.
Main Methods:
- Preparation of 2-exo-Vinyl-7-alkylidenenorbornanes via Diels-Alder reaction.
- Thermal Cope rearrangement of the norbornane adducts.
Main Results:
- Smooth Cope rearrangement observed at elevated temperatures.
- Formation of diverse hexahydroazulene derivatives achieved.
Conclusions:
- Cope rearrangement provides an efficient route to hexahydroazulenes.
- This method expands the synthetic utility of fulvene Diels-Alder adducts.
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