Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 24, Pages 12637-12649Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4022265
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Funding
- Spanish Ministry of Science and Innovation (MICINN) [CTQ2010-18208, CTQ2010-11423-E]
- Xunta de Galicia [10PXIB2200222PR]
- FEDER
- MEC
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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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