Porphyrin-o-quinones as model systems for electron transfer and catecholase reactions

European Journal of Organic Chemistry

Volumn , Issue 12, 2000, Pages 2303-2314

  Speck, Marcus ^a   Kurreck, Harry ^a   Senge, Mathias O ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Electron transfer; Oxygenations; Photosynthesis; Porphyrinoids; Quinones

Indexed keywords

PORPHYRIN DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; MOLECULAR MODEL; PHOTOSYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033919388     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200006)2000:12<2303::AID-EJOC2303>3.0.CO;2-U     Document Type: Article

References (66)

1. [1a] D. Gust, T. A. Moore, Adv. Photochem. 1991, 16, 1-65.
2. [1b] M. R. Wasielewski, Chem. Rev. 1992, 92, 435-461.
3. [1c] H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929-947; Angew. Chem. Int. Ed. Engl. 1995, 34, 849-866.
4. [1c] H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929-947; Angew. Chem. Int. Ed. Engl. 1995, 34, 849-866.
5. [1d] J. S. Connolly, J. R. Bolton, in: Photoinduced Electron Transfer Part D (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, p. 303-393.
6. [2a] J. L. Y. Kong, P. A. Loach, J. Heterocycl. Chem. 1980, 17, 737-744.
7. [2b] D. Gust, T. A. Moore, P. A. Liddell, G. A. Nemeth, L. R. Makings, A. L. Moore, D. Barrett, P. J. Pessiki, R. V. Bensasson, M. Rougée, C. Chachaty, F. C. De Schryver, M. van der Auweraer, A. R. Holzwarth, J. S. Connolly, J. Am. Chem. Soc. 1987, 109, 846-856.
8. [3a] J. von Gersdorff, M. Huber, H. Schubert, D. Niethammer, B. Kirste, M. Plato, K. Möbius, H. Kurreck, R. Eichberger, R. Kietzmann, F. Willig, Angew. Chem. 1990, 102, 690-692; Angew. Chem. Int. Ed. Engl. 1990, 29, 670-672.
9. [3a] J. von Gersdorff, M. Huber, H. Schubert, D. Niethammer, B. Kirste, M. Plato, K. Möbius, H. Kurreck, R. Eichberger, R. Kietzmann, F. Willig, Angew. Chem. 1990, 102, 690-692; Angew. Chem. Int. Ed. Engl. 1990, 29, 670-672.
10. [3b] H. A. Staab, J. Weiser, M. Futscher, G. Voit, A. Rückemann, C. Anders, Chem. Ber. 1992, 125, 2285-2301.
11. [4a] J. Dalton, L. R. Milgrom, J. Chem. Soc., Chem. Commun. 1979, 609-610.
12. [4b] R. A. Cormier, M. R. Posey, W. L. Bell, H. N. Fonda, J. S. Connolly, Tetrahedron 1989, 45, 4831-4843.
13. [4c] J. L. Sessler, M. R. Johnson, Recl. Trav. Chim. Pays-Bas 1987, 106, 222.
14. S. Runge, M. O. Senge, Z. Naturforsch. 1998, 53b, 1021-1030.
15. [6a] H. Dieks, M. O. Senge, B. Kirste, H. Kurreck, J. Org. Chem. 1997, 62, 8666-8680.
16. [6b] R. A. Cormier, M. R. Posey, W. L. Bell, H. N. Fonda, J. S. Connolly, Tetrahedron 1989, 45, 4831-4843.
17. [6c] M. R. Wasielewski, M. P. Niemczyk, D. G. Johnson, W. A. Svec, D. W. Minsek, Tetrahedron 1989, 45, 4785-4806.
18. K. M. Giangiacomo, P. L. Dutton, Proc. Natl. Acad. Sci. USA 1989, 86, 2658-2662.
19. T. Nagaoka, S. Okazaki, T. Fujinaga, J. Electroanal. Chem. 1982, 133, 89-99.
20. [9a] H. Kurreck, S. Aguirre, S. N. Batchelor, H. Dieks, J. von Gersdorff, C. V. M. Kay, H. Mößler, H. Newman, D. Niethammer, J. Schlüpmann, J. Sobek, M. Speck, T. Stabingis, L. Sun, P. Tian, A. Wiehe, K. Möbius, Sol. Energy Mat. Sol. Cells 1995, 38, 91-110.
21. [9b] M. Speck, M. O. Senge, A. Schäfer, H. Kurreck, Bioorg. Med. Chem. Lett. 1997, 7, 2589-2592.
22. G. R. Deviprasad, B. Keshavan, F. D'Souza, J. Chem. Soc., Perkin Trans. 1 1998, 3133-3135.
23. J. von Gersdorff, B. Kirste, H. Kurreck, Liebigs Am. Chem. 1993, 897-903.
24. J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney, A. M. Marguerettaz, J. Org. Chem. 1987, 52, 827-836.
25. A. Rieche, H. Gross, E. Höft, Chem. Ber. 1960, 93, 88-94.
26. [14a] H. Fisher, W. Neumann, Justus Liebigs Ann. Chem. 1932, 494, 225-245.
27. [14b] J. W. Buchler, L. Puppe, Justus Liebigs Ann. Chem. 1970, 740, 142-163.
28. R. Hollenstein, W. von Philipsborn, Helv. Chim. Acta 1973, 56, 320-322.
29. The complete assignment of all resonances can be found in: M. Speck, Synthese, Reaktionen und Strukturanalyse kovalent verknüpfter Perphyrin-o-chinone als Modellverbindungen für die Photosynthese, Shaker Verlag, 1999, p. 334. ISBN 3-8265-4600-8.
30. The dihedral angles were determined from a single crystal X-ray structure analysis of the the protected porphyrin catechols. M. O. Senge, M. Speck, A. Wiehe, S. Aguirre, H. Dieks, H. Kurreck, Photochem. Photobiol. 1999, 70, 206-216.
31. [18a] M. E. Peover, J. Chem. Soc. 1962, 4540-4549.
32. [8b] O. Ryba, J. Pilar, J. Petránek, Coll. Czech. Chem. Commun. 1968, 33, 26-34.
33. [19a] D. Rehm, A. Weller, Ber. Bunsenges. Phys. Chem. 1969, 73, 834-839.
34. [19b] D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259-271.
35. [20a] M. R. Wasielewski, M. P. Niemczyk, J. Am. Chem. Soc. 1984, 106, 5043-5045.
36. [20b] H. A. Staab, G. Voit, J. Weiser, M. Futscher, Chem. Ber. 1992, 125, 2303-2310.
37. Oriel Corporation, 1-kW Hg(Xe) lamp type 977B0010.
38. T. Funabiki, "Oxygenases in Model Systems" in: Catalysis by Metal Complexes Series (Ed.: T. Funabiki), Kluwer Academic Publishers, Norwell, 1996, p. 408.
39. [23a] C. Kashima, A. Tomotake, Y. Omote, J. Heterocycl. Chem. 1987, 24, 785-788.
40. [23b] T. Funabiki, M. Ishikawa, Y. Nagai, J. Yorita, S. Yoshida, J. Chem. Soc., Chem. Commun. 1994, 1951-1952.
41. [23c] L. S. White, E. J. Hellman, L. Que, Jr., J. Org. Chem. 1982, 47, 3766-3769.
42. A comprehensive overview about possible oxidation products of pyrocatechol is given in: [24a] Y. Tatsuno, C. Nakamura, T. Saito, J. Mol. Catal. 1987, 42, 57-66. [24b] T. Funabiki, A. Mizoguchi, T. Sugimoto, S. Yoshida, Chem. Lett. 1983, 917-920.
43. A comprehensive overview about possible oxidation products of pyrocatechol is given in: [24a] Y. Tatsuno, C. Nakamura, T. Saito, J. Mol. Catal. 1987, 42, 57-66. [24b] T. Funabiki, A. Mizoguchi, T. Sugimoto, S. Yoshida, Chem. Lett. 1983, 917-920.
44. T. Funabiki, T. Yamazaki, A. Fukui, T. Tanaka, S. Yoshida, Angew. Chem. 1998, 110, 527-530; Angew. Chem. Int. Ed. 1998, 37, 513-515.
45. T. Funabiki, T. Yamazaki, A. Fukui, T. Tanaka, S. Yoshida, Angew. Chem. 1998, 110, 527-530; Angew. Chem. Int. Ed. 1998, 37, 513-515.
46. L. Que, Jr., in: Iron Carriers and Iron Proteins (Ed.: T. M. Loehr), VCH, New York, 1989, p. 467.
47. H. Tomioka, H. Fukao, Y. Izawa, Bull. Chem. Soc. Jpn. 1978, 51, 540-543.
48. [28a] O. Hayaishi, M. Katagiri, S. Rothberg, J. Am. Chem. Soc. 1955, 77, 5450-5451.
49. [28b] O. Hayaishi, M. Katagiri, S. Rothberg, J. Biol. Chem. 1957, 229, 905-920.
50. G. Speier, Z. Tyeklar, Chem. Ber. 1979, 112, 389-391.
51. [30a] G. O. Schenck, K. G. Kinkel, H.-J. Mertens, Justus Liebigs Ann. Chem. 1953, 584, 125-155.
52. [30b] C. S. Foote, Y. C. Chang, R. W. Denny, J. Am. Chem. Soc. 1970, 92, 5216-5218.
53. H. H. Wasserman, J. R. Scheffer, J. Am. Chem. Soc. 1967, 89, 3073-3075.
54. [32a] H. H. Wasserman, J. L. Ives, Tetrahedron 1981, 37, 1825-1852.
55. [32b] W. Adam, Chem.-Ztg. 1975, 99, 142-155.
56. [32c] D. R. Kearns, Chem. Rev. 1971, 71, 395-427.
57. C. F. Wilcox, M. P. Stevens, J. Am. Chem. Soc. 1962, 84, 1258-1262.
58. [34a] G. A. Russen, R. L. Blankespoor, J. Mattox, P. R. Whittle, D. Symalla, J. R. Dodd, J. Am. Chem. Soc. 1974, 96, 7249-7254.
59. [34b] V. Jayathirtha, V. Ramamurthy, E. Schaumann, H. Nimmesgern, J. Org. Chem. 1984, 49, 615-621.
60. R. Ramasseul, A. Rassat, Bull. Soc. Chim. Fr. 1963, 2218-2219.
61. J. Weinstock, D. L. Ladd, J. W. Wilson, C. K. Brush, N. C. F. Yim, G. Gallagher, M. E. McCarthy, Jr., J. Silvestri, H. M. Sarau, K. E. Flaim, D. M. Ackerman, P. E. Setler, A. J. Tobia, R. A. Hahn, J. Med. Chem. 1986, 29, 2315-2325
62. The original procedure of Lindsey was modified to assure complete neutralization of the reaction mixture. The higher basicity had no negative influence on the overall yield of the porphyrin.
63. D. L. Comins, J. D. Brown, J. Org. Chem. 1984, 49, 1078-1083.
64. To investigate compound 1 immediately after demetalation, the reaction was performed in deuterated chloroform.
65. R. Kuhn, I. Hammer, Chem. Ber. 1950, 83, 413-414.
66. The assignment of the isomers was confirmed by non broad-band decoupled NMR spectra.