Temperature controlled syn-anti conformational switching in zinc containing porphyrin dimers via ligand assistance

Tetrahedron Letters

Volumn 40, Issue 27, 1999, Pages 5051-5054

  Borovkov, Victor V ^a   Lintuluoto, Juha M ^a   Inoue, Yoshihisa ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN; ZINC;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; DIMERIZATION; THERMOSTABILITY;

EID: 0033516549     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00931-4     Document Type: Article

References (39)

1. (a) Casella, L. and Colonna, S. in Metalloporphyrins Catalyzed Oxidations, Montanari, F. and Casella,L. eds., Kluwer Academic Publisher, Dordrecht, 1994, pp. 307-340;
2. (b) Gentemann, S.; Medforth, C. J.; Forsyth, T. P.; Nurco, D. J.; Smith, K. M.; Fajer, J.; Holten, D. J. Am. Chem. Soc., 1994, 116, 7363;
3. (c) Medforth, C. J.; Senge, M. O.; Smith, K. M.; Sparks, L. D.; Shelnutt, J. A. J. Am. Chem. Soc., 1992, 114, 9859.
4. (a) Burrell, A. K.; Officer, D. L.; Reid, D. C. W.; Wild, K. Y. Angew. Chem., Int. Ed. Engl., 1998, 37, 114;
5. (b) Arnold, D. P.; Borovkov, V. V.; Ponomarev, G. V. Chem. Lett., 1996, 485;
6. (c) Iseki, Y.; Inoue, S. J. Chem. Soc., Chem. Commun., 1994, 2577;
7. (d) Bonfantini, E. E.; Officer, D. L. J. Chem. Soc., Chem. Commun., 1994, 1445.
8. (a) Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. submitted for publication;
9. (b) Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. Synlett, 1998, 768;
10. (c) Ponomarev, G. V.; Yashunsky, D. V.; Borovkov, V. V.; Sakata, Y.; Arnold, D. Russ. Chem. Heterocycl. Comp., 1997, 1627;
11. (d) Sugiura, K.-i.; Ponomarev, G.; Okubo, S.; Tajiri, A.; Sakata, Y. Bull. Chem. Soc. Jpn., 1997, 70, 1115.
12. (a) Ponomarev, G. V.; Borovkov, V. V.; Sugiura, K.-i.; Sakata, Y.; Shul'ga, A. M. Tetrahedron Lett., 1993, 34, 2153;
13. (b) Senge, M. O.; Gerzevske, K. R.; Vicente, M. G. H.; Forsyth, T. P.; Smith, K. M. Angew. Chem., Int. Ed. Engl., 1993, 32, 750;
14. (c) Osuka, A.; Nakajima, S.; Maruyama, K. J. Org. Chem., 1992, 57, 7355;
15. (d) Karaman, R.; Blaskó, A.; Almarsson, Ö.; Arasasingham, R.; Bruice, T. C. J. Am. Chem. Soc., 1992, 114, 4889.
16. (a) Abraham, R. J.; Eivazi, F.; Pearson, H.; Smith, K. M. J. Chem. Soc., Chem. Commun., 1976, 698;
17. (b) Abraham, R. J.; Eivazi, F.; Pearson, H.; Smith, K. M. J. Chem. Soc., Chem. Commun., 1976, 699.
18. Hunter, C. A.; Meah, M. N.; Sanders, J. K. M. J. Am. Chem. Soc., 1990, 112, 5773.
19. Chernook, A. V.; Shulga, A. M.; Zenkevich, E. I.; Rempel, U.; von Borczyckowski, C. J. Phys. Chem., 1996, 100, 1918.
20. Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem., 1965, 11, 371.
21. (a) Zhou, X.; Chan, K. S. J. Org. Chem., 1998, 63, 99;
22. (b) Sessler, J. L.; Capuano, V. L. Tetrahedron Lett., 1993, 34, 2387;
23. (c) Osuka, A.; Tanabe, N.; Zhang, R.-P.; Maruyama, K. Chem. Lett., 1993, 1-505.
24. (a) Shultz, D. A.; Gwaltney, K. P.; Lee, H. J. Org. Chem., 1998, 63, 4034;
25. (b) Arnold, D. P.; James, D. A. J. Org. Chem., 1997, 62, 3460;
26. (c) Lin, V. S.-Y.; Dimagno, S. G.; Therien, M. J. Science, 1994, 264, 1105;
27. d) Anderson, H. L. Inorg. Chem., 1994, 33, 972.
28. (a) Higuchi, H.; Shimizu, K.; Takeuchi, M.; Ojima, J.; Sugiura, K.-i.; Sakata, Y. Bull. Chem. Soc. Jpn., 1997, 70, 1923;
29. (b) Kitagawa, R.; Kai, Y.; Ponomarev, G. V.; Sugiura, K.-i.; Borovkov, V. V.; Kaneda, T.; Sakata, Y. Chem. Lett., 1993, 107 1.
30. Yoshida, N.; Shimidzu, H.; Osuka, A. Chem. Lett., 1998, 55.
31. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett., 1998, 39, 2993.
32. (a) Knapp, S.; Vasudevan, J.; Emge, T. J.; Arison, B. H.; Potenza, J. A.; Schugar, H. J. Angew. Chem., Int. Ed. Engl., 1998, 37, 2368;
33. (b) Kobuke, Y.; Miyaji, H. J. Am. Chem. Soc., 1994, 116, 4111.
34. (a) Arai, T.; Takei, K.; Nishino, N.; Fujimoto, T. Chem. Commun., 1996, 2133;
35. (b) Akins, D. L.; Zhu, H.-R. Guo, C. J. Phys. Chem., 1994, 98, 3612;
36. (c) van Esch, J. H.; Feiters, M. C.; Peters, A. M.; Nolte, R. J. M. J. Phys. Chem., 1994, 98, 5541;
37. (d) Schick, G. A.; Schreiman, I. C.; Wagner, R. W.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc., 1989, 111, 1344.
38. 3OD (24:1). The thermodynamic parameters (ΔH, ΔS and ΔG of this equilibrium will be reported in the forthcoming article, Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. J. Phys. Chem., 1999, in press.
39. Shul'ga, A. M.; Ponomarev, G. V. Russ. Chem. Heterocycl. Comp., 1988, 339.