Synthesis of Cyano-Substituted Diaryltetracenes from Tetraaryl[3]cumulenes

Date

2014-09-11

Author

Gawel, Przemyslaw
Dengiz, Çağatay
Finke, Aaron D.
Trapp, Nils
Boudon, Corinne
Gisselbrecht, Jean-Paul
Diederich, Francois

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https://scg.ch/component/phocadownload/category/174-scs-fall-meeting-2014
https://hdl.handle.net/11511/97211

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Swiss Chemical Society Fall Meeting 2014

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Department of Chemistry, Conference / Seminar

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Synthesis of Cyano-Substituted Diaryltetracenes from Tetraaryl[3] cumulenes**

GAWEL, Przemyslaw; Dengiz, Çağatay; FINKE, Aaron D.; TRAPP, Nils; BOUDON, Corinne; GISSELBRECHT, Jean-Paul; DIEDERICH, Francois (2014-04-22)

A versatile, two-step synthesis of highly substituted, cyano-functionalized diaryltetracenes has been developed, starting from easily accessible tetraaryl[3]cumulenes. This unprecedented transformation is initiated by [2+2] cycloaddition of tetracyanoethylene (TCNE) to the proacetylenic central double bond of the cumulenes to give an intermediate zwitterion, which after an electrocyclization cascade and dehydrogenation yields 5,5,11,11-tetracyano-5,11-dihydrotetracenes in a one-pot procedure. A subsequent c...
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Citation Formats

P. Gawel et al., “Synthesis of Cyano-Substituted Diaryltetracenes from Tetraaryl[3]cumulenes,” presented at the Swiss Chemical Society Fall Meeting 2014, 2014, Accessed: 00, 2022. [Online]. Available: https://scg.ch/component/phocadownload/category/174-scs-fall-meeting-2014.