We thank the National Science Foundation and the Petroleum Research Fund administered by the American Chemical Society for support.
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Communication
The Isomers of [12]Annulyne and their Reactive Relationships to Heptalene and Biphenyl†
Article first published online: 2 OCT 2008
DOI: 10.1002/anie.200803863
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Rose, Brad D., Reiter, Richard C. and Stevenson, Cheryl D. (2008), The Isomers of [12]Annulyne and their Reactive Relationships to Heptalene and Biphenyl. Angew. Chem. Int. Ed., 47: 8714–8718. doi: 10.1002/anie.200803863
- †
Publication History
- Issue published online: 21 OCT 2008
- Article first published online: 2 OCT 2008
- Manuscript Received: 5 AUG 2008
Funded by
- National Science Foundation
- Petroleum Research Fund
- Abstract
- Article
- References
- Cited By
Keywords:
- annulene;
- EPR spectroscopy;
- heptalene;
- NMR spectroscopy;
- radical anions
[12]Annulyne not like benzyne: The base-initiated condensation of hexadiyne in nonpolar solvents leads directly to the symmetrical isomers of [12]annulyne, i.e. the all cis isomer, which exists as its cumulene, and the 6,9-trans,trans isomer. One-electron transfer to this mixture leads to the formation of an unsymmetrical [12]annulyne radical anion, which transfers an electron to the all cis system leading to the biphenyl radical anion, while reduction of the other isomer leads to heptalene (see scheme).