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Synfacts 2008(4): 0361-0361  
DOI: 10.1055/s-2008-1042845
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Six-Electron Organic Redox System

Contributor(s): Timothy M. Swager, Jeewoo Lim
Z. Han, T. P. Vaid*, A. L. Rheingold
Washington University, St. Louis and University of California, San Diego, USA
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

The authors describe a synthesis of hexacation 1 6+ via cobalt-mediated cyclotrimeri­zation of bis(4-pyridyl)acetylene. This approach is more concise than the previously-reported synthesis of the methyl derivative of 1 6+ (G. A. Crispino, R. Breslow J. Org. Chem. 1992, 57, 1849). Furthermore, the authors were the first to recognize the molecule’s capability to undergo a six-electron reduction to the radialene-like 1 0.