Journal
SYNLETT
Volume 26, Issue 11, Pages 1633-1637Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1381005
Keywords
arynes; polycyclic aromatic hydrocarbons; acenes; Diels-Alder reaction; cycloadditions
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Funding
- Spanish Ministry of Science and Competitiveness (MINECO) [CTQ2013-44142-P, MAT2013-46593-C6-6-P]
- European Union [610446]
- Xunta de Galicia [GPC2014/25]
- FEDER
- Spanish Ministry of Education
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Large polycyclic o-(trimethylsilyl)aryl triflates are easily obtained by reaction of commercially available bisaryne precursors with cyclopentadienones. The transformation involves controlled generation of one of the aryne functionalities, trapping by Diels-Alder reaction with a dienone, and chelotropic extrusion of CO. The newly synthesized triflates are precursors of acene-based arynes, including a didehydropentacene.
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