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Synfacts 2010(6): 0649-0649
DOI: 10.1055/s-0029-1219982
DOI: 10.1055/s-0029-1219982
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Radialene Synthesis
Contributor(s):Timothy M. Swager, D. Barney WalkerS. Shinozaki, T. Hamura, Y. Ibusuki, K. Fujii, H. Uekusa, K. Suzuki*
SORST, JST Agency, Tokyo, Tokyo Institute of Technology, Kwansei Gakuin University, Sanda and PRESTO, JST Agency, Tokyo, Japan
Hexaradialenes by Successive Ring Openings of Tris(alkoxytricyclobutabenzenes): Synthesis and Characterization
Angew. Chem. Int. Ed. 2010, 49: 3026-3029
SORST, JST Agency, Tokyo, Tokyo Institute of Technology, Kwansei Gakuin University, Sanda and PRESTO, JST Agency, Tokyo, Japan
Hexaradialenes by Successive Ring Openings of Tris(alkoxytricyclobutabenzenes): Synthesis and Characterization
Angew. Chem. Int. Ed. 2010, 49: 3026-3029
Further Information
Publication History
Publication Date:
20 May 2010 (online)
Key words
tricyclobutabenzenes - ring opening - radialenes
Significance
The authors present a remarkable synthetic route to hexaradialene 1 that utilizes a thermally-driven ring-opening isomerization reaction to form the six exocyclic double bonds in the final step. The reaction proceeds efficiently provided that sufficiently bulky groups are tethered to the triannulated parent compound prior to isomerization, with both the syn and the anti precursors converted into 1.
Comment
Alicyclic cross-conjugated molecules of this type are rare and further studies on the reactivity of these intriguing molecules could provide new routes to novel polycyclic aromatic systems.