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Synfacts 2007(6): 0601-0601  
DOI: 10.1055/s-2007-968586
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A Heterocycle That Switches Between Aromatic and Antiaromatic

Contributor(s): Timothy M. Swager, Eric L. Dane
S. Miao, P. v. R. Schleyer, J. I. Wu, K. I. Hardcastle, U. H. F. Bunz*
Georgia Institute of Technology, Atlanta; University of Georgia, Athens; Emory University, Atlanta, USA
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

In an attempt to synthesize 1, the authors were surprised to recover and separate a mixture of 1 and 2. Both compounds are red, fluorescent, crystalline solids, stable to chromatography and they can be interconverted by redox reactions. Compound 2 represents a 16-π-electron system that can be considered antiaromatic, but unlike most other antiaromatic ring systems it appears relatively stable, slowly converting over weeks back into 1 by air oxidation.