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Synthesis of 8-bromo-5,12-tetracenequinone and 2-bromotetracene derivatives

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Abstract

A series of bromotetracenequinones 1 and bromotetracenes 2 were prepared from 4-bromophthalic anhydride. The parent tetracenequinone 1a and tetracene 2a were sparingly soluble in organic solvents. In contrast, dipropyl-substituted tetracenequinone 1b and tetracene 2b were a little more soluble. Preparation of dihexyl-substituted tetracene 2c proved to be difficult. Sonogashira coupling of 1b with trimethylsilylacetylene afforded the corresponding product.

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References

  1. M. Bendikov, F. Wudl, D.F. Perepichka, Chem. Rev. 104, 4891–4945 (2004)

    Article  CAS  Google Scholar 

  2. J.E. Anthony, Angew. Chem. Int. Ed. 47, 452–483 (2008)

    Article  CAS  Google Scholar 

  3. Z. Chen, P. Muller, T.M. Swager, Org. Lett. 8, 273–276 (2006)

    Article  CAS  Google Scholar 

  4. T. Seri, H. Qu, L. Zhou, K. Kanno, T. Takahashi, Chem. Asian J. 3, 388–392 (2008)

    Article  CAS  Google Scholar 

  5. C.-H. Lin, K.-H. Lin, B. Pal, L.-D. Tsou, Chem. Commun. 803–805 (2009)

  6. K. Ito, T. Suzuki, Y. Sakamoto, D. Kubota, Y. Inoue, F. Sato, S. Tokito, Angew. Chem. Int. Ed. 42, 1159–1162 (2003)

    Article  CAS  Google Scholar 

  7. J.A. Merio, C.R. Newman, C.P. Geriach, T.W. Kelley, D.V. Muyres, S.E. Fritz, M.F. Toney, C.D. Frisbie, J. Am. Chem. Soc. 127, 3997–4009 (2005)

    Article  Google Scholar 

  8. A.M. Müller, Y.S. Avlasevich, W.W. Schoeller, K. Müllen, C.J. Bardeen, J. Am. Chem. Soc. 129, 14240–14250 (2007)

    Article  Google Scholar 

  9. T. Kimoto, K. Tanaka, Y. Sakai, A. Ohno, K. Yoza, K. Kobayashi, Org. Lett. 11, 3658–3661 (2009)

    Article  CAS  Google Scholar 

  10. F. Diederich, P.J. Stang, Metal-catalyzed cross-coupling reactions (Wiley-VCH, Weinheim, 1998)

    Book  Google Scholar 

  11. J.S. Meek, F.M. Dewey, J. Org. Chem. 35, 1315–1318 (1970)

    Article  CAS  Google Scholar 

  12. J.F.W. McOmie, D.H. Perry, Synthesis 248, 416–417 (1973)

    Article  Google Scholar 

  13. S. Coffey, V. Boyd, J. Chem. Soc., 2468–2470 (1954)

  14. C. Kitamura, T. Ohara, A. Yoneda, T. Kawase, T. Kobayashi, H. Naito, Chem. Lett. 40, 58–59 (2011)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by Grants-in-Aid for Scientific Research (nos. 23550161 and 23108720) from JSPS and MEXT.

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Authors and Affiliations

  1. Department of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo, 671-2280, Japan

    Chitoshi Kitamura, Naohiro Taka & Takeshi Kawase

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  1. Chitoshi Kitamura
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  2. Naohiro Taka
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  3. Takeshi Kawase
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Correspondence to Chitoshi Kitamura.

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Kitamura, C., Taka, N. & Kawase, T. Synthesis of 8-bromo-5,12-tetracenequinone and 2-bromotetracene derivatives. Res Chem Intermed 39, 139–146 (2013). https://doi.org/10.1007/s11164-012-0638-2

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  • DOI: https://doi.org/10.1007/s11164-012-0638-2

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