The Bicorannulenyl Dianion: A Charged Overcrowded Ethylene

Super bowl: Bicorannulenyl, a large biaryl composed of two corannulene bowls, effectively becomes an overcrowded ethylene upon reduction to form a dianion (see picture). DFT calculations and NMR spectroscopic experiments reveal the double‐bond character of the connection between the two bowls. Three...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2010-10, Vol.49 (41), p.7538-7542
Main Authors: Eisenberg, David, Jackson, Edward A., Quimby, Jennifer M., Scott, Lawrence T., Shenhar, Roy
Format: Article
Language:English
Subjects:
annulenes
carbanions
conformation analysis
conjugation
overcrowded ethylenes
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Summary:Super bowl: Bicorannulenyl, a large biaryl composed of two corannulene bowls, effectively becomes an overcrowded ethylene upon reduction to form a dianion (see picture). DFT calculations and NMR spectroscopic experiments reveal the double‐bond character of the connection between the two bowls. Three stable diastereomers that interconvert through bowl inversions and central bond rotations were shown to exist.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201002515