Synthesis of regiospecifically meso-functionalized tetraarylporphyrins via arylbis(2-pyrrolyl)methanes

Gazzetta Chimica Italiana

Volumn 126, Issue 3, 1996, Pages 179-185

  Banfi, Stefano ^a,b   Manfredi, Amedea ^a,b   Pozz, Gianluca ^a,b   Quici, Silvio ^a,b   Trebicka, Artan ^a,b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF TIRANA   (Albania)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000640804     PISSN: 00165603     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. P.R. ORTIZ DE MONTELLANO, Ed., «Cytochrome P-450, structure, mechanism and biochemistry», Plenum Press, New York and London, 1986;
2. I. TABUSHI, Coord. Chem. Rev., 86, 1 (1988);
3. B. MEUNIER, Chem. Rev., 92, 1411 (1992).
4. F. MONTANARI, L. CASELLA, Eds., «Metalloporphyrins catalyzed oxidations», Kluwer Acad. Publ., Dordrecht, 1994;
5. S. QUICI, S. BANFI, G. Pozzi, Gazz. Chim. Ital, 123, 597 (1993 ).
6. J.P. GROVES, R.S. MYERS, J. Am. Chem. Soc., 105, 5791 (1983);
7. Y. NARUTA, F. TANI, N. ISHIHARA, K. MARUYAMA, ibid., 113, 6865 (1991);
8. S. O'MALLEY, T. KODADEK, J. Am. Chem. Soc., Ill, 9116 (1989);
9. R.L. HALTERMAN, S.-T. JAN, J. Org. Chem., 56, 5253 (1991);
10. S. VILAIN, P. MAILLARD, M. MOMENTEAU, J. Chem. Soc., Chem. Commun., 1697 (1994);
11. P. Le MAUX, H. BAHRI, G. SIMONNEAUX, J. Chem. Soc., Chem. Commun., 1287 (1994);
12. M. VEYRAT, O. MAURY, F. FAVERJON, D.E. OVER, R. RAMASSEUL, J.-C. MARCHON, I. TUROWSKA-TYRK, W.R. SCHRIDT, Angew. Chem., Internat. Ed., 33, 220 (1994).
13. I. TABUSHI, S. KUGIMIYA, M.G. KINNAIRD, T. SASAKI, J. Am. Chem. Soc., 107, 4192 (1985);
14. C.A. HUNTER, M.N. MEAH, J.K.M. SANDERS, J. Chem. Soc., Chem. Commun., 694 (1988);
15. LP. DANKS, T.G. LANE, I.O. SUTHERLAND, M. YAP, Tetrahedron, 48, 7679 (1992);
16. T. MIZUTANI, T. EMA, T. TOMITA, Y. KURODA, H. OGOSHI, J. Chem. Soc., Chem. Commun., 520 (1993);
17. C.M. DRAIN, R. FISCHER, E.G. NOLEN, J.-M. LEHN, ibid., 243 (1993).
18. a) A. OSUKA, K. MARUYAMA, Chem. Lett., 825 (1987);
19. b) S. CHARDON-NOBLAT, J.-P. SAUVAGE, P. MATHIS, Angew. Chem., Internat. Ed., 28, 593 (1989);
20. J. DAVILA, A. HARRIMAN, L.R. MILGROM, Chem. Phys. Lett., 136, 427 (1987);
21. S. PRATHAPAN, T.E. JOHNSON, J.S. LINDSEY, J. Am. Chem. Soc., 115, 7519 (1993);
22. e) J.S. LINDSEY, S. PRATHAPAN, T.E. JOHNSON, R.W. WAGNER, Tetrahedron, 50, 8941 (1994);
23. f) H.L. ANDERSON, S.J. MARTIN, D.D.C. BRADLEY, Angew. Chem., Internat. Ed., 33, 655 (1994).
24. P. ROTHEMUND, A.R. MENOTTI, J. Am. Chem. Soc., 63, 267 (1941).
25. A.D. ADLER, F.R. LONGO, W. SHERGELIS, J. Am. Chem. Soc., 86, 3145 (1964).
26. A.M. D'A. ROCHA GONSALVES, M.M. PEREIRA, J. Heterocycl. Chem., 22, 931 (1985);
27. A.M. D'A. ROCHA GONSALVES, J.M.T B. VAREJAO, M.M. PEREIRA, ibid., 28, 635 (1991).
28. a) J.S. LINDSEY, I.e. SCHREIMAN, HC. Hsu, P.C. KEARNEY, A.M. MARGUERETTAZ, J. Org. Chem., 52, 827 (1987);
29. b) A.W. VAN DER MADE, E.J.H. HOPPENBROUWER, R.J.M. NOLTE, W. DRENTH, Reel. Trav. Chim. Pays-Bas, 107, 15 (1988);
30. J.S. LINDSEY, K.A. MACCRUM, J.S. TYHONAS, Y.-Y. CHUANG, J. Org. Chem., 59, 579 (1994);
31. A.M. D'A. ROCHA GONSALVES, M.M. PEREIRA, A.C. SERRA, R.A.W. JOHNSTONE, M.L.P. NUNES, J. Chem. Soc., Perkin Trans., 1, 2053 (1994).
32. J.P. COLLMAN, C.M. ELLIOTT, T.R. HALBERT, B. TOVROG, Proc. Natl. Acad. Sci. USA, 74, 18 (1977).
33. P.L. ANELLI, S. BANFI, F. LEGRAMANDI, F. MONTANARI, G. Pozzi, S. Quid, J. Chem. Soc., Perkin Trans. I, 1345 (1993);
34. S. BANFI, F. MON-ANARI, G. Pozzi, S. QUICI, Tetrahedron, SO, 9025 (1994).
35. a) M. BADGER, R.D. JONES, R.L. LASLETT, Austr. J. Chem., 17, 1157 (1964);
36. b) J.L. SESSLER, A. MOZAFFARI, M.R. JOHNSON, Org. Synth., 70 68 (1992).
37. D.L. BOGER, R.S. COLEMAN, J.S. PANEK, D. YOHANNES, J. Org. Chem., 49, 4405 (1984).
38. S. BANFI, R. MANDELLI, F. MONTANARI, S. QUICI, Gazz. Chim. Ital, 123, 409 (1995).
39. L. WEINSTOCK, R.J. TULL, U.S. Patent, 3,423,475; C.A., 70, P 87266h (1969).
40. F.D. BELLAMY, K. Ou, Tetrahedron Lett., 25, 839 (1984).
41. W.B. AUSTIN, N. BILOW, W.J. KELLEGHAN. K.S.Y. LAU, J. Org. Chem., 46, 2280 (1981).
42. D.M. WALLACE, K.M. SMITH, Tetrahedron Lett., 31, 7265 (1990).
43. A. OSUKA, T. NAGATA, F. KOBAYASHI, K. MARUYAMA, J. Heterocyd. Chem., 27, 1657 (1990);
44. J-I. SETSUNE, M. HASHIMOTO, J. Chem. Soc., Chem. Commun., 657 (1994);
45. D.A. LEE, J.M. BRISSON, KM. SMITH, Heterocydes, 40, 131 (1995).
46. M.J. GUNTER, L.N. MANDER, J. Org. Chem., 46, 4792 (1981).
47. J.L. SESSLER, Angew. Chem., Internat. Ed., 33, 1348 (1994);
48. P.J. CHMIELEWSKI, L. LATOS-GRAZYNSKI, K. RACHLEWICZ, T. GLOWIAK, ibid., 33, 779 (1994).
49. R.M. WILSON, A. HENGGE, J. Org. Chem., 52, 2699 (1987);
50. C.-H. LEE, J.S. LINDSEY, Tetrahedron, 50, 11427 (1994).
51. G. CASIRAGHI, M. CORNIA, G. RASSU, C. DEL SANTE, P. SPANU, Tetrahedron, 48, 5619 (1992).