N-methyl-substituted aza[1(n)]metacyclophane: Preparation, structure, and properties

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8236-8241

  Ito, Akihiro ^a   Ono, Yukiharu ^a   Tanaka, Kazuyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; METACYCLOPHANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; ELECTROCHEMISTRY; ORGANIC CHEMISTRY;

EID: 0033615584     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990983m     Document Type: Article

References (66)

1. (a) Iwamura, H. Pure Appl. Chem. 1987, 59, 1595.
2. (b) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179.
3. Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88.
4. Iwamura, H. Pure Appl. Chem. 1993, 65, 57.
5. (e) Borden, W. T.; Iwamura, H.; Berson, J. A. Acc. Chem. Res. 1994, 24, 109.
6. (f) Rajca, A. Chem. Rev. 1994, 94, 871.
7. Forrester, A. R.; Hay, J. M.; Thomson, R. H. Organic Chemistry of Stable Free Radicals; Academic Press: New York, 1968.
8. (a) Yoshizawa, K.; Tanaka, K.; Yamabe, T. Chem. Lett. 1990, 1311.
9. (b) Ishida, T.; Iwamura, H. Chem. Lett. 1991, 317.
10. Yoshizawa, K.; Tanaka, K.; Yamabe, T.; Yamauchi, J. J. Chem. Phys. 1992, 96, 5516.
11. Yoshizawa, K.; Takata, K.; Tanaka, K.; Yamabe, T. Polym. J. 1992, 24, 857.
12. (e) Ito, A.; Yoshizawa, K.; Tanaka, K.; Yamabe, T. Solid State Commun. 1993, 87, 935.
13. (f) Ito, A.; Ota, K.; Tanaka, K.; Yamabe, T.; Yoshizawa, K. Macromolecules 1995, 28, 5618.
14. (g) Yoshizawa, K.; Hoffmann, R. Chem. Eur. J. 1998, 1, 403.
15. (h) Goto, H.; Iino, K.; Akagi, K.; Shirakawa, H. Synth. Met. 1997, 85, 1683.
16. (a) Rajca, A.; Rajca, S.; Padmakumar, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2091.
17. (b) Rajca, A.; Rajca, S.; Desai, S. R. J. Am. Chem. Soc. 1995, 117, 806.
18. Rajca, A.; Lu, K.; Rajca, S. J. Am. Chem. Soc. 1997, 119, 10335.
19. Rajca, A.; Wongsriratanakul, J.; Rajca, S. J. Am. Chem. Soc. 1997, 119, 11674.
20. (e) Rajca, A.; Wongsriratanakul, J.; Rajca, S.; Cerny, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1229.
21. (a) Diederich, F. Cyclophanes; Monograghs in Supramolecular Chemistry; Royal Society of Chemistry: London, 1991.
22. (b) Vögtle, F. Cyclophane Chemistry; Wiley: Chichester, 1993.
23. (a) Gutsche, C. D. Calixarenes; Monographs in Supramolecular Chemistry; Royal Society of Chemistry: London, 1989.
24. (b) Izatt, R. M.; Bradshaw, J. S.; Pawlak, K.; Bluening, R. L.; Tarbet, B. J. Chem. Rev. 1992, 92, 1261.
25. Shinkai, S. Tetrahedron 1993, 49, 8933.
26. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
27. (e) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713.
28. (a) König, B.; Rödel, M.; Bubenitschek, P.; Jones, P. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 661.
29. (b) König, B.; Rödel, M.; Bubenitschek, P.; Jones, P. G.; Thondorf, I. J. Org. Chem. 1995, 60, 7406.
30. Mascal, M.; Richardson, J. L.; Blake, A. J.; Li, W.-S. Tetrahedron Lett. 1997, 38, 7639.
31. Nakayama, J.; Katano, N.; Sugihara, Y.; Ishii, A. Chem. Lett. 1997, 897.
32. (e) Katano, N.; Sugihara, Y.; Ishii, A.; Nakayama, J. Bull. Chem. Soc. Jpn. 1998, 71, 2695 and references therein.
33. (f) Avarvari, N.; Mézailles, N.; Ricard, L.; Le Floch, P.; Mathey, F. Science 1998, 280, 1587.
34. (g) Abd-El-Aziz, A. S.; de Denus, C. R.; Zaworotko, M. J.; Sharma, C. V. K. Chem. Commun. 1998, 265.
35. (h) Baxter, I.; Colquhoun, H. M.; Hodge, P.; Kohnke, F. H.; Williams, D. J. Chem. Commun. 1998, 283.
36. Baxter, I.; Colquhoun, H. M.; Hodge, P.; Kohnke, F. H.; Williams, D. J. Chem. Commun. 1998, 1991.
37. (j) Fruend, T.; Kübel, C.; Baumgarten, M.; Enkelmann, V.; Gherghel, L.; Reuter, R.; Müllen, K. Eur. J. Org. Chem. 1998, 555, 5.
38. (a) Beller, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1316.
39. (b) Hartwig, J. F. Synlett 1997, 329.
40. Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
41. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
42. (e) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
43. (a) Kambara, T.; Izumi, K.; Nakadani, Y.; Narise, T.; Hasegawa, K. Chem. Lett. 1997, 1185.
44. (b) Louie, J.; Hartwig, J. F.; Fry, A. J. J. Am. Chem. Soc. 1997, 119, 11695.
45. Yang, M.-H.; Lin, T.-W.; Chou, C.-C.; Lee, H.-C.; Chang, H.-C.; Lee, G.-H.; Leung, M.-K.; Peng, S.-M. Chem. Commun. 1997, 2279.
46. Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 4960.
47. (e) Goodson, F. E.; Hartwig, J. F. Macromolecules 1998, 31, 1700.
48. (f) Spetseris, N.; Ward, R. E.; Meyer, T. Y. Macromolecules 1998, 31, 3158.
49. Ito, A.; Ono, Y.; Tanaka, K. New J. Chem. 1998, 779.
50. All the calculations were performed with the Gaussian 94 suite of programs: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, P. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
51. Becke, A. D. Phys. Rev. 1988, A38, 3098.
52. Perdew, J. P. In Electronic Structure of Solids; Ziesche, P., Eschrig, H., Eds.; Akademie Verlag: Berlin, 1991.
53. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
54. Bondi, A. J. Phys. Chem. 1964, 68, 441.
55. Unfortunately, only disordered crystals of 3 have been grown, and to date, we have failed to refine the molecular structure completely even by a low-temperature measurement. Benzene rings are orientationally disordered upward and downward to the plane defined by three nitrogen atoms. Hence, the conformation of 3 is hardly determined. Only two [1.1.1]metacyclophanes have been determined to adopt the partial cone conformation by X-ray analysis:
56. (a) Sergeev, V. A.; Ovchinnikov, Yu. E.; Nedel'kin, V. I.; Astankov, A. V.; Andrianova, O. B.; Shklover, V. E.; Zamaev, I. A.; Struchkov, Yu. T. Bull. Acad. Sci. USSR Div. Chem. Sci. 1998, 37, 1440.
57. (b) Yoshida, M.; Goto, M.; Nakanishi, F. Organometallics 1999, 18, 1465.
58. A usefulness of the strain analysis using these isodesmic reactions was suggested by one of the reviewers of this paper. For isodesmic reactions, see ref 14.
59. Wolinski, K.; Hilton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
60. Yano, M.; Sato, K.; Shiomi, D.; Ichimura, A.; Abe, K.; Takui, T.; Itoh, K. Tetrahedron Lett. 1996, 37, 9207.
61. (a) Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587.
62. (b) Borden, W. T. In Diradicals; Borden, W. T., Ed. Wiley: New York, 1982.
63. A reviewer has remarked that replacement of the N-methyl group by the other one without hydrogens improves the irreversible redox behavior of the present system. This may be another way to realize the high-spin azacyclophanes.
64. Willstätter, R.; Pfennenstiel, A. Chem. Ber. 1905, 38, 2244.
65. Snyder, H. R.; Heckert, R. E. J. Am. Chem. Soc. 1952, 74, 2006.
66. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348.