Journal
TETRAHEDRON
Volume 57, Issue 17, Pages 3715-3724Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00240-X
Keywords
stilbene-like photocyclizations; polycyclic aromatic hydrocarbon systems; divergent-convergent syntheses; phenacenes
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Iterative strategies are reported for the synthesis of some large monodisperse [Il]phenacenes, which an polycyclic aromatic hydrocarbon derivatives having n benzene rings fused in an extended phenanthrene-like structural motif. The key carbon-carbon bond-forming steps involve either Wittig or McMurry coupling reactions to give diarylethylenes, and oxidative photocyclizations of those diarylethylenes. tert-Butyl substituents on the phenacene framework serve as solubilizing groups. (C) 2001 Elsevier Science Ltd. All rights reserved.
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