Oligofurans linked by a rigid tether undergo tandem cycloaddition reactions with high stereoselectivity. The reaction of bisfurans with dimethyl acetylenedicarboxylate (DMAD) involves tandem [4 + 2]/[4 + 2] cycloadditions in a pincer mode. The reaction of oligofurans with arynes involves stereoselective tandem [4 + 2]/[4 + 2] cycloaddition reactions in a domino mode. The corresponding aryne adducts have been transformed into extended perylene derivatives by deoxygenation and aromatization with HCl/EtOH.
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| http://dx.doi.org/10.1021/jo4022265 | DOI Listing |
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