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Synfacts 2011(2): 0159-0159  
DOI: 10.1055/s-0030-1259246
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Synthesis of Tetrabenzocoronenes

Contributor(s): Timothy M. Swager, Stefanie A. Sydlik
X. Zhang, X. Jiang*, K. Zhang, L. Mao, J. Luo, C. Chi, H. S. O. Chan, J. Wu*
National University of Singapore, Singapore and Zhejiang University, Hangzhou, P. R. of China
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Publikationsverlauf

Publikationsdatum:
19. Januar 2011 (online)

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Significance

The authors synthesized types of contorted tetrabenzocoronenes (TBCs). The Barton-Kellogg reaction (1 → 2 and 4 → 5) is used to creatively extend the core structure efficiently (59-89% yield). The final intermolecular ­cyclodehydrogenation was found to be most efficiently carried out in two steps, as the photo-cyclization would not yield the fully cyclized TBC, even after extended reaction times.