5H,13H-5,13a-[1′,2′]benzenocyclopenta[rst]pentaphen-13-one: A new triptycene derivative with a strained structure

Chemistry Letters

Volumn 36, Issue 4, 2007, Pages 540-541

  Kurata, Hiroyuki ^a   Kyusho, Masahiro ^a   Nishimae, Yuichi ^a   Matsumoto, Kouzou ^a   Kawase, Takeshi ^a   Oda, Masaji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34248554170     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.540     Document Type: Article

References (25)

1. a) G. Yamamoto, Y. Kobayashi, K. Ono, E. Yano, M. Minoura, Y. Mazaki, Bull. Chem. Soc. Jpn. 2006, 79, 1293.
2. b) C. Zhang, C.-F. Chen, J. Org. Chem. 2006, 71, 6626.
3. c) E. M. Veen, P. M. Postma, H. T. Jonkman, A. L. Spek, B. L. Feringa, Chem. Commun. 1999, 1709.
4. d) J.-S. Yang, T. M. Swager, J. Am. Chem. Soc. 1998, 120, 11864.
5. e) T. M. Long, T. M. Swager, J. Am. Chem. Soc. 2003, 125, 14113.
6. a) G. S. Kottas, L. I. Clarke, D. Horinek, J. Michl, Chem. Rev. 2005, 105, 1281.
7. b) T. R. Kelly, R. A. Silva, H. D. Silva, S. Jasmin, Y. Zhao, J. Am. Chem. Soc. 2000, 122, 6935.
8. c) C. E. Godinez, G. Zepeda, M. A. Garcia-Garibay, J. Am. Chem. Soc. 2002, 124, 4701.
9. a) H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, R. Lapouyade, Chem. Soc. Rev. 2000, 29, 43.
10. b) H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, R. Lapouyade, Chem. Soc. Rev. 2001, 30, 248.
11. a) H.-D. Becker, K. Sandros, K. Andersson, Angew. Chem., Int. Ed. Engl. 1983, 22, 495.
12. b) H.-D. Becker, K. Andersson, Tetrahedron Lett. 1983, 24, 3273.
13. c) H.-D. Becker, H. Sorensen, E. Hammarberg, Tetrahedron Lett. 1989, 30, 989.
14. d) H. Sakurai, K. Sakamoto, A. Nakamura, M. Kira, Chem. Lett. 1985, 497.
15. e) J. Luo, H. Hart, J. Org. Chem. 1987, 52, 3631.
16. Y. Nishimae, H. Kurata, M. Oda, Angew. Chem. Int. Ed. 2004, 43, 4947.
17. H.-D. Becker, L. Hansen, K. Andersson, J. Org. Chem. 1986, 51, 2956.
18. 1H NMR spectra of all new compounds and crystallographic data and structures of 1, 3, and 7 are summerized in Supporting Information, which is available electronically on the CSJ-Journal web site; http://www.csj.jp/journals/chem-lett/.
19. max/nm (log ε) 384 (3.85), 364(3.89), 347(3.71), 331(3.42), 256(5.18).
20. Crystallographic data of 1, 3, and 7 have been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-637053, 637054, and 637055, respectively.
21. There should be four isomers for the dimer of 1; however, two of them are excluded because of steric hindrance (see Supporting Information, which is available electronically on the CSJ-Journal web site; http://www.csj.jp/ journals/chem-lett/).
22. Examples of approaches to selective formation of anthracene cross-dimers: a) H. Bouas-Laurent, R. Lapouyade, J. Chem. Soc. D 1969, 817.
23. b) D. Bailey, V. E. Williams, Chem. Commun. 2005, 2569.
24. c) D. Bailey, V. E. Williams, J. Org. Chem. 2006, 71, 5778.
25. V. Ramamurthy, K. Vekatesan, Chem. Rev. 1987, 87, 433.