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Synfacts 2010(3): 0293-0293
DOI: 10.1055/s-0029-1219261
DOI: 10.1055/s-0029-1219261
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Encircling the Square: Synthesis of Quadrannulene
Contributor(s):Timothy M. Swager, D. Barney Walker Bharat, R. Bhola, T. Bally, A. Valente, M. K. Cyrański, Ł. Dobrzycki, S. M. Spain, P. Rempała, M. R. Chin, B. T. King*
University of Nevada, Reno, USA; University of Fribourg, Switzerland; University of Warsaw, Poland; Universität Duisburg-Essen, Germany
Quadrannulene: A Nonclassical Fullerene Fragment
Angew. Chem. Int. Ed. 2010, 49: 399-402
University of Nevada, Reno, USA; University of Fribourg, Switzerland; University of Warsaw, Poland; Universität Duisburg-Essen, Germany
Quadrannulene: A Nonclassical Fullerene Fragment
Angew. Chem. Int. Ed. 2010, 49: 399-402
Further Information
Publication History
Publication Date:
18 February 2010 (online)
Key words
fullerenes - corannulenes - cyclotrimerization
Significance
The authors report the first synthesis of a [4]circulene. Quadrannulene 1 is comprised of a central four-membered ring fused together with four benzenoid units. Unlike previously reported bowl-shaped annulenes, such as coronene, this structural motif is not observed in classical graphitic structures.
Comment
Despite the highly strained central core of 1 the compound is remarkably stable suggesting that new families of arenes and fullerenes could be accessed using this methodology.