Synthesis of 3,4-Bis(benzylidene)cyclobutenes

Author(s)
Swager, Timothy Manning; Parkhurst, Rebecca Rosenberg
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Abstract
The syntheses of several derivatives of 3,4-bis(benzylidene)cyclobutene are reported. Previously unknown 1,2-dibromo-3,4-bis(benzylidene)cyclobutene was obtained through in situ generation of 1,6-diphenyl-3,4-dibromo-1,2,4,5-tetraene followed by electrocyclic ring closure. Ensuing reduction and metal-catalyzed cross-coupling provided additional derivatives. The effects of ring strain on the geometry and electronics of these derivatives were examined by X-ray crystallography and ¹H NMR spectroscopy, respectively.
Date issued
2011-11
URI
http://hdl.handle.net/1721.1/74245
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Synlett
Publisher
Thieme Publishing Group
Citation
Parkhurst, Rebecca, and Timothy Swager. “Synthesis of 3,4-Bis(benzylidene)cyclobutenes.” Synlett 2011.11 (2011): 1519–1522.
Version: Author's final manuscript
ISSN
0936-5214
1437-2096
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