Synthesis and catalytic reactivity of D4-symmetric dinorbornabenzene-derived metallotetraarylporphyrins

Tetrahedron

Volumn 53, Issue 33, 1997, Pages 11257-11276

  Halterman, Ronald L ^a   Jan, Shyi Tai ^a   Nimmons, Heather L ^a   Standlee, David J ^a   Khan, Masood A ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4,5,6,7,8 OCTAHYDRO 1:4,5:8 DIMETHANOANTHRACENE 9 CARBOXYALDEHYDE; 1,4 BENZOQUINONE; ACETAL; ALKENE; BENZALDEHYDE; CYCLOPENTADIENE DERIVATIVE; DINORBORNABENZENE DERIVATIVE; HYPOCHLORITE SODIUM; MANGANESE CHLORIDE; METAL COMPLEX; METALLOTETRAARYLPORPHYRIN; PORPHYRIN DERIVATIVE; PYRROLE; TETRAARYLPORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DIASTEREOISOMER; EPOXIDATION; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS; TURNOVER TIME; X RAY DIFFRACTION;

EID: 0030750342     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00729-1     Document Type: Article

References (48)

1. Hydrogenation: (a) review: Koenig, K. E. in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985; Vol 5, p 71.
2. (b) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori, R. J. Am. Chem. Soc. 1987, 109, 1596.
3. Epoxidation: (c) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
4. (d) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
5. (e) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
6. (a) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801-2803.
7. (b) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296-2298.
8. (c) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063-7064.
9. (d) Irie, R.; Noda, K.; Ito, Y.; Katsuki, T. Tetrahedron Lett. 1991, 32, 1055-1058.
10. (e) Lee, N. H.; Muci, A. R.; Jacobsen, E. N. Tetrahedron Lett. 1991, 32, 5055-5058.
11. (a) Review: Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411.
12. (b) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834-3835.
13. (c) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628.
14. (d) Naruta, Y.; Tani, F.; Ishihara, N.; Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865-6872.
15. (e) Renaud, J.-P.; Battioni, P.; Mansuy, D. New J. Chem. 1987, 11, 279-290.
16. (f) Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791-5796.
17. O'Malley, S.; Kodadek, T. J. Am. Chem. Soc. 1989, 111, 9116-9117.
18. Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834-3835.
19. Halterman, R. L.; Jan, S.-T. J. Org. Chem. 1991, 56, 5253.
20. Barry, J.; Kodadek, T. Tetrahedron Lett. 1994, 35, 2465-2468.
21. Halterman, R. L.; Jan, S.-T.; Nimmons, H. L. Synlett. 1991, 791-792.
22. Alder, K.; Stein, G. Liebigs Ann. Chemie 1933, 501, 247.
23. Dehn, W. M.; Jackson, K. E. J. Am. Chem. Soc. 1933, 55, 4284.
24. Rieche, A.; Gross, H.; Höft, E. Chem. Ber. 1960, 93, 88.
25. Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250.
26. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y.L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Horikawa, K.; Wang, Z.-M. Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
27. (b) McKee, B. H.; Gilheany, D. G.; Sharpless, K. B. Org. Synth. 1991, 70, 47.
28. Mash, E. A.; Nelson, K. A. J. Am. Chem. Soc. 1985, 107, 8256.
29. (a) Wagner, R. W.; Lawrence, D. S.; Lindsey, J. S Tetrahedron Lett. 1987, 28, 3069.
30. (b) Lindsey, J. S.; Wagner, R. W. J. Org. Chem. 1989, 54, 828.
31. Halterman, R. L.; Mei, X.Tetrahedron Lett. 1996, 37, 6291.
32. Adler, A. D.; Longo, F. R.; Kampas, F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 32, 2443.
33. Chatterjee, A.; Fleisher, E. B.; Palmer, J. M.; Srivastova, T. S. J. Am. Chem. Soc. 1971, 93, 3162.
34. Kaizu, Y.; Misu, N.; Tsuji, K.; Kaneko, Y.; Kobayashi, H. Bull Chem. Soc. Jpn. 1985, 58, 103.
35. X-ray diffraction-derived structure obtained by Dr. M. Khan, departmental crystallographer at Univ. of Oklahoma.
36. Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Tanaka, H.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980-7984.
37. (a) Imuta, M.; Ziffer, H. J. Org. Chem. 1978, 43, 4540.
38. (b) Boyd, D. R.; Sharma, N. D.; Smith, A. E. J. Chem. Soc., Perkin Trans. I 1982, 2767.
39. (a) Harvey, R. G. Synthesis 1986, 605-619.
40. (b) Benasutti, M.; Ezzedine, D.; Loechler, E. L. Chem. Res. Toxicol. 1988, 1, 162.
41. Banfi, S.; Montanari, F.; Quid, S. J. Org. Chem. 1989, 54, 1850-1859.
42. Naruta, Y.; Tani, F.; Maruyama, K. Tetrahedron Asymm. 1991, 2, 533.
43. Toda, F.; Tanka, K.; Nagamatsu, S.; Tetrahedron Lett. 1984, 25, 4929.
44. Bartley, D. W.; Kodadek, T. J. Tetrahedron Lett. 1990, 31, 6303-6306.
45. (a) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
46. (b) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
47. 13C NMR spectra for porphyrin (+)-1 and key intermediates in its synthesis can be found in the Supplementary Material in reference 6.
48. For general experimental methods and instrumentation details used in our laboratory see: Halterman, R. L.; Ramsey, T. M. J. Organomet. Chem. 1994, 465, 175.