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Synfacts 2008(2): 0150-0150  
DOI: 10.1055/s-2007-992430
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A Functionalization of Pro-cata Positions of Pentacene

Contributor(s): Timothy M. Swager, Gaku Fukuhara
J. E. Anthony*, J. Gierschner, C. A. Landis, S. R. Parkin, J. B. Sherman, R. C. Bakus, II
University of Kentucky, Lexington, USA and University of Mons-Hainaut, Mons, Belgium
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

The authors are able to synthesize pentacene derivatives 7a-d. Dioxolane-functionalized pentacenes are easily synthesized by classical methods from known catechol 1. Acetal formation yields a mixture of diester 2 and anhydride 3, which is reduced to provide dimethanol 4 in good yield. Oxidation followed by condensation with 1,4-cyclohexanedione yields quinone 6, which is reduced to the corresponding pentacene 7.