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Synfacts 2006(7): 0672-0672  
DOI: 10.1055/s-2006-941870
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Stable Isobenzofurans

Contributor(s): Timothy M. Swager, Scott Meek
Y.-L. Chen, C.-K. Hau, H. Wang, H. He, M.-S. Wong, A. W. M. Lee
Hong Kong Baptist University, P. R. of China
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

The synthesis of two stable, oxadisilole-fused isobenzofurans is reported. Trapping of the benzynes derived from benzobioxadi­silole and benzotrioxadisilole via fluoride-induced desilylation with furan gave the corresponding epoxynaphthalenes. Reaction of these compounds with 3,6-di-2-pyridyl-1,2,4,5-tetrazine afforded the desired isobenzofurans in good yields. The isobenzofurans proved reasonably stable at room temperature, surviving column chromatography over silica gel and providing sharp melting points. Various linear acenes were also synthesized by condensation of the isobenzofurans with DMAD and various benzyne derivatives followed by dehydration with LiAlH4.