Related Experiment Video
Updated: Oct 18, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Hemicryptophane Cages with a C1-Symmetric Cyclotriveratrylene Unit
Chunyang Li1, Anne-Doriane Manick1, Marion Jean1
1Aix Marseille Univ, CNRS, Centrale Marseille iSm2, 13284 Marseille, France.
Abstract:
Two new hemicryptophanes combining a cyclotriveratrylene unit with either an aminotrisamide or a tris(2-aminoethyl)amine (tren) moiety have been synthesized. Although a conventional synthesis approach was used, the molecular cages obtained are devoid of the expected C3 symmetry. NMR analyses and X-ray crystal structure determination showed that these hemicryptophanes exhibited C1 symmetry due to the unusual arrangement of the substituents of the cyclotriveratrylene unit. This unprecedented arrangement is related to a change in the regioselectivity of the Friedel-Crafts reactions that led to the CTV cap. This constitutes an original approach to access enantiopure chiral molecular cages with low symmetry.
Related Concept Videos
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Thermal and Photochemical Electrocyclic Reactions: Overview
Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
Stereoisomerism of Cyclic Compounds
Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous...

