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Synfacts 2015; 11(1): 0029
DOI: 10.1055/s-0034-1379668
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Taking the Dimers Out of Diazaheptacenes

Contributor(s):
Timothy M. Swager
,
Sarah P. Luppino
Engelhart JU, Tverskoy O, Bunz UH. F * Ruprecht-Karls-Universität Heidelberg, Germany
A Persistent Diazaheptacene Derivative.

J. Am. Chem. Soc. 2014;
136: 15166-15169
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

azaaromatics - palladium - aromatic chemistry

Significance

The authors have successfully designed, synthesized, and isolated the first persistent azaheptacene. The diazaheptacene in this work required four Si(s-Bu)3-ethynyl groups to effectively prevent dimerization upon oxidizing to the final product 4.


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Comment

The key synthetic step was the fast oxidation using manganese oxide to convert 3 into 4, which was carried out for no longer than forty seconds. The product 4 was stable for approximately one hour, after which dimerization products were detected. Alternative trialkylsilyl-ethynyl groups, such as the TIPS-ethynyl group, proved ineffective at impeding dimerization.


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