Synthesis of novel polycyclic aromatic hydrocarbons by transannular cyclization Tobe Laboratory M1 Yamane Hiroshi Contents Introduction ・Polycyclic Aromatic Hydrocarbons Cyclization Reaction ・Examples of Cyclization Reaction ・Continuous Cyclization Reaction ・Transannular Cyclization Reaction My Project Conclusion ~Introduction~ Polycyclic Aromatic Hydrocarbon (PAH) PAH・・・多環状芳香族化合物 picene K - Doped 20K Superconducting materials Kubozono, Y. et al. Nature, 2010, 464, 76-79. 9,9’-bifluorenylidene Electron Acceptors of Lightweight Organic devices Wudl, F. et al. Angew. Chem. Int. Ed. 2009, 49, 532-536. ~Cyclization reaction~ Examples of Cyclization Reaction Zander, M. et al. J. Chem. Soc. 1957, 4616–4619. Scheme 1. Diels-Alder reaction Bednya, N. P. et al. Zh. Obshch. Khim. 1937, 7, 2919–2924. Scheme 2. Friedel-Crafts reaction Müllen, K. et al. Chem. Ber. 1991, 124, 2091–2100. Scheme 3. Oxidative and reductive reaction ~Cyclization reaction~ Bergman Cyclization Reaction Scheme 4. Bergman reaction Bergman, R. G. et al., J. Am. Chem. Soc. 1972. 94. 660. Colkins, T. L. Tetrahedron Lett. 1992, 33, 2315-2318. ~Cyclization reaction~ Tandem Cyclization Reaction by Electrophile and Radical Reagent Tandem Cyclization・・・連続環化 Lutz, V. et al. Angew. Chem. Int. Ed. 2003, 42, 5757−5760. Ghiviriga, I. et al. J. Am. Chem. Soc. 2008, 130, 11535–11545. Scheme 5. Cyclization by electrophilic and radical reagent ~Cyclization reaction~ Transannular Cyclization Reaction of [10]annulene Transannular cyclization・・・渡環環化 Scheme 6. Electrophilic reaction of dinaphtho[10]annulene Tobe. Y, Org. Lett. 2009, 11, 4104–4106. Scheme 7. Two synthetic methods of Zethrene Clar, E. et al. Chem. Ber. 1955, 88, 1520 Sondheimer, F. et al. J. Am. Chem. Soc., 1968, 90,530–531 ~Cyclization reaction~ Transannular Cyclization Reaction of [14]annulene butadiyne Scheme 8. Nucleophilic reaction of dehydrotribenzo[14]annulene My Project butadiyne Scheme 9. Transannular cyclization reaction of tetrabenzo[14]annulene Conclusion ・Recently, PAHs are expected to be the functionalized organic materials. ・Transannular cyclization reaction is considered of value for synthetic method to novel PAHs. ・Tetrabenzo[14]annulene that is target compound has been synthesized.
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