Stereogenic motif consisting of rigid ring and intraannular chains: Isolation and structures of stereoisomers of 9-alkyl-1,8-anthrylene- butadiynylene cyclic dimers

Organic Letters

Volumn 11, Issue 2, 2009, Pages 321-324

  Toyota, Shinji ^a   Onishi, Hiroyuki ^a   Kawai, Yoshihiro ^a   Morimoto, Takaaki ^a   Miyahara, Hiroaki ^a   Iwanaga, Tetsuo ^a   Wakamatsu, Kan ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

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EID: 62149107312     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802488z     Document Type: Article

References (25)

1. Part 11 of "Chemistry of Anthracene-Acetylene Oligomers." For part 10, see: (a) Toyota, S.; Miyahara, H.; Goichi, M.; Wakamatsu, K.; Iwanaga, T. Bull. Chem. Soc. Jpn. 2008, 81, 1147.
2. (a) Sadowy, A. L.; Tykwinski, R. R. Modern Supramolecular Chemistry; Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2008; Chapter 6.
3. (b) Zhang, W.; Moore, J. S. Angew. Chem., Int. Ed. 2006, 45, 4416.
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5. (d) Khan, A.; Kaiser, C.; Hecht, S. Angew. Chem., Int. Ed. 2006, 45, 1878.
6. (e) Marsden, J. A.; Palmer, G. J.; Haley, M. M. Eur. J. Org. Chem. 2003, 2355.
7. (f) Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807.
8. (a) Toyota, S.; Goichi, M.; Kotani, M. Angew. Chem., Int. Ed. 2004, 43, 2248.
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12. Toyota, S.; Kurokawa, M.; Araki, M.; Nakamura, K.; Iwanaga T Org. Lett. 2007, 9, 3655.
13. For example, Höger, S.; Weber, J.; Leppert, A.; Enkelmann, V. Beilstein J. Org. Chem. 2008, 4, 1.
14. (b) Fischer, M.; Höger, S. Tetrahedron 2003, 59, 9441.
15. (a) The parent compound of this framework is known. Akiyama, S.; Misumi, S.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1960, 33, 1293.
16. (b) This system was recently applied to organic phototransistors. Zhao, W.; Tang, Q.; Chan, H. S.; Xu, J.; Lo, K. Y.; Miao, Q. Chem. Commun. 2008, 4324.
17. House, H. O.; Hrabie, J. A.; VanDerveer, D. J. Org. Chem. 1986, 51, 921.
18. 5 for dehydration, the reaction product was contaminated by a large amount of 9-alkylidene isomers.
19. Katz, H. E. J. Org. Chem. 1989, 54, 2179.
20. -3 mol/L. The yield was not significantly affected by the concentration so much as long as the organic reactant was dissolved in the solvent.
21. X-ray data of syn-3b are given in Supporting Information. As for 3b and 3c, the less polar nature of the anti forms is attributed to their centrosymmetric structure leading to zero or a negligibly small value of the dipole moment, while the syn forms are noncentrosymmetric.
22. -1, T= 113 K, 6933 independent reflections, R1 = 0.0586, wR2 = 0.1035, GOF = 0.95, CCDC 705747.
23. The extent of folding is evaluated from the torsion angles of the C(4a)-C(9a)-C(9)-C(12) chain (see Figure 3a) and other corresponding sites. For example, the folding angles are 25° and 30° for 1,8-dichloro-9-methyl- and 1,8,9-tribromo-anthracenes. (a) Delleca, R. J.; Penfold, B. R.; Robinson, W. T. Acta Crystallogr., Sect. B: Struct. Sci. 1980, 25B, 1589.
24. (b) Akiba, K.; Yamashita, M.; Yamamoto, Y.; Nagase, S. J. Am. Chem. Soc. 1999, 121, 10644.
25. Sample of 3c was significantly decomposed by heating for a longer time or at higher temperature.