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Synfacts 2008(11): 1161-1161  
DOI: 10.1055/s-0028-1083478
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Diels-Alder Synthesis of Trisbicyclo[2.2.1]heptabenzene

Contributor(s): Timothy M. Swager, Rebecca R. Parkhurst
Z.-Q. Gao, J.-F. Wei*, X.-Y. Shi, J. Yu
Shaanxi Normal University, P. R. of China
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Publication Date:
23 October 2008 (online)

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Significance

The authors report the synthesis of a cyclohexatriene containing trisbicyclo[2.2.1]heptabenzene that does not involve highly reactive organometallic intermediates. The critical step involves a triple Diels-Alder cycloaddition between the tri-diene formed from 1,3,4,6,7,9-hexabromotrindane and dimethyl but-2-ynedioate. The desired product 3 was obtained in 32% yield. The structure of trans-3 was confirmed by X-Ray crystal structural analysis.