A simple hybrid cyclyne consisting of 1,3-diethynylbenzene and ether units: Synthesis and novel AG+-induced cyclization leading to the perylene skeleton formation [10]

Journal of the American Chemical Society

Volumn 122, Issue 30, 2000, Pages 7404-7405

  Yamaguchi, Yoshihiro ^a   Kobayashi, Shigeya ^a   Wakamiya, Tateaki ^a   Matsubara, Yoshio ^a   Yoshida, Zen Ichi ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; ETHER DERIVATIVE; SILVER;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; LETTER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS;

EID: 0034596336     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000822w     Document Type: Letter

References (26)

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2. For example: (a) Newkome, G. R.; Lee, H.-W. J. Am. Chem. Soc. 1983, 105, 5956. (b) Ransohoff, J. E. B.; Staab, H. A. Tetrahedron Lett. 1985, 26, 6179. (c) Dobler, M.; Dumic, M.; Egli, M.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1985, 24, 792. Lehn, J.-M. Angew. Chem., Int. Ed Engl. 1988, 27, 89. (e) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009. (f) Bell, T. W.; Guzzo, F.; Drew, M. G. B. J. Am. Chem. Soc. 1991, 113, 3115. (g) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227.
3. For example: (a) Newkome, G. R.; Lee, H.-W. J. Am. Chem. Soc. 1983, 105, 5956. (b) Ransohoff, J. E. B.; Staab, H. A. Tetrahedron Lett. 1985, 26, 6179. (c) Dobler, M.; Dumic, M.; Egli, M.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1985, 24, 792. Lehn, J.-M. Angew. Chem., Int. Ed Engl. 1988, 27, 89. (e) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009. (f) Bell, T. W.; Guzzo, F.; Drew, M. G. B. J. Am. Chem. Soc. 1991, 113, 3115. (g) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227.
4. For example: (a) Newkome, G. R.; Lee, H.-W. J. Am. Chem. Soc. 1983, 105, 5956. (b) Ransohoff, J. E. B.; Staab, H. A. Tetrahedron Lett. 1985, 26, 6179. (c) Dobler, M.; Dumic, M.; Egli, M.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1985, 24, 792. Lehn, J.-M. Angew. Chem., Int. Ed Engl. 1988, 27, 89. (e) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009. (f) Bell, T. W.; Guzzo, F.; Drew, M. G. B. J. Am. Chem. Soc. 1991, 113, 3115. (g) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227.
5. For example: (a) Newkome, G. R.; Lee, H.-W. J. Am. Chem. Soc. 1983, 105, 5956. (b) Ransohoff, J. E. B.; Staab, H. A. Tetrahedron Lett. 1985, 26, 6179. (c) Dobler, M.; Dumic, M.; Egli, M.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1985, 24, 792. Lehn, J.-M. Angew. Chem., Int. Ed Engl. 1988, 27, 89. (e) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009. (f) Bell, T. W.; Guzzo, F.; Drew, M. G. B. J. Am. Chem. Soc. 1991, 113, 3115. (g) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227.
6. For example: (a) Newkome, G. R.; Lee, H.-W. J. Am. Chem. Soc. 1983, 105, 5956. (b) Ransohoff, J. E. B.; Staab, H. A. Tetrahedron Lett. 1985, 26, 6179. (c) Dobler, M.; Dumic, M.; Egli, M.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1985, 24, 792. Lehn, J.-M. Angew. Chem., Int. Ed Engl. 1988, 27, 89. (e) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009. (f) Bell, T. W.; Guzzo, F.; Drew, M. G. B. J. Am. Chem. Soc. 1991, 113, 3115. (g) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227.
7. For example: (a) Newkome, G. R.; Lee, H.-W. J. Am. Chem. Soc. 1983, 105, 5956. (b) Ransohoff, J. E. B.; Staab, H. A. Tetrahedron Lett. 1985, 26, 6179. (c) Dobler, M.; Dumic, M.; Egli, M.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1985, 24, 792. Lehn, J.-M. Angew. Chem., Int. Ed Engl. 1988, 27, 89. (e) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009. (f) Bell, T. W.; Guzzo, F.; Drew, M. G. B. J. Am. Chem. Soc. 1991, 113, 3115. (g) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227.
8. (h) Pak, J. J.; Timothy, J. R.; Haley, M. M. J. Am. Chem. Soc. 1999, 121, 8182.
9. (i) Youngs, W. J.; Tessier, C. A.; Bradshow, J. D. Chem. Rev. 1999, 99, 3153.
10. f (AM1 for given and reference compounds. The MM2 structure of 3 was almost the same as its X-ray structure.
11. Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403.
12. We are currently trying to synthesize 2 by the quite different strategy. The results will be reported in due course.
13. -1) 2918, 2906, 2862, 2231, 1477, 1434, 1373, 1253, 1074, 1033, 887, 792, 680, 557.
14. 3) δ 1.89 (tt, J = 6.6, 6.9 Hz, 8H), 2.68 (t, J = 6.9 Hz, 8H), 3.32 (t, J = 6.6 Hz, 8H), 6.98 (s, 2H), 7.00 (d, J = 8.4 Hz, 4H), 7.19 (t, J = 8.4 Hz, 2H); MS (EI, 70 eV) m/z 352, 203, 190, 176, 158, 143, 132, 117, 105, 91, 79, 41; HRMS (EI, 70 eV) calcd 352.2402, found 352.2407.
15. int = 0.015). 151 variables [I > 2σ(I)].
16. Nishinaga, T.; Kawamura, T.; Komatsu, K. J. Chem. Soc., Chem. Commun. 1998, 2263.
17. Bennett, M. A.; Schwemlein, H. P. Angew. Chem., Int. Ed. Engl. 1989, 28, 1296.
18. -1) 2960, 2923, 2854, 1261, 1097, 1056, 1024, 806, 669, 518; MS (EI, 70 eV) m/z 336, 307, 280, 138, 40; HRMS (EI, 70 eV) calcd 336.1150, found 336.1158.
19. int = 0.040), 143 variables [I > - 10.00σ(I)].
20. Jong, T.-T.; Leu, S.-J. J. Chem. Soc., Perkin Trans. 1 1990, 423.
21. Ning, G. L.; Munakata, M.; Wu, L. p.; Maekawa, M.; Suenaga, Y.; Kuroda-Sowa, T.; Sugimoto, K. Inorg. Chem. 1999, 38, 5668 and literature cited herein.
22. Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Sac. 1997, 119, 4578.
23. Bradshaw, J. D.; Soloocki, D.; Tessier, C. A.; Youngs, W. J. J. Am. Chem. Soc. 1994, 116, 3177.
24. (a) Schön, J. H.; Kloc, Ch.; Bucher, E.; Batlogg, B. Nature 2000, 403, 408.
25. (b) Schön, J. H. Private communication on the intercolumn distance before and after doping.
26. Synthesis and properties of S and Si analogues of 6 will be reported in due course.