- Short and efficient synthesis of coronene derivatives via ruthenium-catalyzed benzannulation protocol
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TpRuPPh3(CH3CN)2PF6 (3 mol %) was very active in catalytic benzannulation of 1-phenyl-2-ethynylbenzenes in dichloroethane (60 °C, 36 h) to afford phenanthrene in 95% yield. This method is applicable to the synthesis of various polycyclic aromatic hydrocarbons via two- and four-fold benzannulations, including various substituted coronene derivatives (53-86% yields) using this catalyst at a moderate loading (10 mol %).
- Shen, Hung-Chin,Tang, Jhih-Meng,Chang, Hsu-Kai,Yang, Chia-Wei,Liu, Rai-Shung
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p. 10113 - 10116
(2007/10/03)
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- Photochemical Intramolecular Acylation of Polycyclic Aromatic o-Dicarboxylic Anhydrides
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The light-induced Diels-Alder addition of maleic anhydride to naphthochrysene (1) yields the same dicarboxylic anhydrides 2 and 4 as the thermal Diels-Alder addition. 4 is further isomerized by light to give the fluorenone carboxylic acid 6, as was revealed by isolation of compounds 7 and 8 after decarboxylation of the mixture 2 + 4.Analogously, 12 is formed by irradiation of the dicarboxylic anhydride 10; decarboxylation of 12 yields 13 and 14.The simpler systems 15 and 17 did not undergo an analogous light-induced isomerization.Photophysical examination of 4, 10, 15, and 17 gave no clue to the reasons for this difference in behaviour.
- Bunte, Reinhard,Gundermann, Karl-Dietrich,Leitich, Johannes,Polansky, Oskar E.,Zander, Maximilian
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p. 3521 - 3527
(2007/10/02)
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