Porphyrins with exocyclic rings. 13. Synthesis and spectroscopic characterization of highly modified porphyrin chromophores with fused acenaphthylene and benzothiadiazole rings

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8455-8469

  Lash, Timothy D ^a   Chandrasekar, Pushpa ^a   Osuma, Augustine T ^a   Chaney, Sun T ^a   Spence, John D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; NICKEL; PORPHYRIN; THIADIAZOLE DERIVATIVE; ZINC;

ARTICLE; CHROMATOPHORE; NUCLEAR MAGNETIC RESONANCE; PHOTOSENSITIZATION; POLYMERIZATION; SPECTROSCOPY; SYNTHESIS;

EID: 0032515121     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9815655     Document Type: Article

References (83)

1. Part 12: Bastian, J. A.; Lash, T. D. Tetrahedron 1998, 54, 6299.
2. Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197.
3. Brown, S. B.; Truscott, T. G. Chem. Br. 1993, 29, 955. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19. Milgrom, L. R.; MacRobert, S. Chem. Br. 1998, 34 (35), 45.
4. Brown, S. B.; Truscott, T. G. Chem. Br. 1993, 29, 955. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19. Milgrom, L. R.; MacRobert, S. Chem. Br. 1998, 34 (35), 45.
5. Brown, S. B.; Truscott, T. G. Chem. Br. 1993, 29, 955. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19. Milgrom, L. R.; MacRobert, S. Chem. Br. 1998, 34 (35), 45.
6. Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975; pp 871-889.
7. Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. See also: May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820.
8. Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. See also: May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820.
9. Baker, E. W.; Palmer, S. E. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1, pp 486-552. Lash, T. D. Energy Fuels 1993, 7, 166. Baker, E. W. J. Am. Chem. Soc. 1966, 88, 2311. Baker, E. W.; Yen, T. F.; Dickie, J. P.; Rhodes, R. E.; Clark, L. F. J. Am. Chem. Soc. 1967, 89, 3631-3639. Kaur, S.; Chicarelli, M. I.; Maxwell, J. R. J. Am. Chem. Soc. 1986, 108, 1347.
10. Baker, E. W.; Palmer, S. E. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1, pp 486-552. Lash, T. D. Energy Fuels 1993, 7, 166. Baker, E. W. J. Am. Chem. Soc. 1966, 88, 2311. Baker, E. W.; Yen, T. F.; Dickie, J. P.; Rhodes, R. E.; Clark, L. F. J. Am. Chem. Soc. 1967, 89, 3631-3639. Kaur, S.; Chicarelli, M. I.; Maxwell, J. R. J. Am. Chem. Soc. 1986, 108, 1347.
11. Baker, E. W.; Palmer, S. E. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1, pp 486-552. Lash, T. D. Energy Fuels 1993, 7, 166. Baker, E. W. J. Am. Chem. Soc. 1966, 88, 2311. Baker, E. W.; Yen, T. F.; Dickie, J. P.; Rhodes, R. E.; Clark, L. F. J. Am. Chem. Soc. 1967, 89, 3631-3639. Kaur, S.; Chicarelli, M. I.; Maxwell, J. R. J. Am. Chem. Soc. 1986, 108, 1347.
12. Baker, E. W.; Palmer, S. E. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1, pp 486-552. Lash, T. D. Energy Fuels 1993, 7, 166. Baker, E. W. J. Am. Chem. Soc. 1966, 88, 2311. Baker, E. W.; Yen, T. F.; Dickie, J. P.; Rhodes, R. E.; Clark, L. F. J. Am. Chem. Soc. 1967, 89, 3631-3639. Kaur, S.; Chicarelli, M. I.; Maxwell, J. R. J. Am. Chem. Soc. 1986, 108, 1347.
13. Baker, E. W.; Palmer, S. E. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1, pp 486-552. Lash, T. D. Energy Fuels 1993, 7, 166. Baker, E. W. J. Am. Chem. Soc. 1966, 88, 2311. Baker, E. W.; Yen, T. F.; Dickie, J. P.; Rhodes, R. E.; Clark, L. F. J. Am. Chem. Soc. 1967, 89, 3631-3639. Kaur, S.; Chicarelli, M. I.; Maxwell, J. R. J. Am. Chem. Soc. 1986, 108, 1347.
14. Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59. See also: Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
15. Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59. See also: Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
16. Lash, T. D.; Novak, B. H. Tetrahedron Lett. 1995, 36, 4381. Novak, B. H.; Lash, T. D. J. Org. Chem. 1998, 63, 3998.
17. Lash, T. D.; Novak, B. H. Tetrahedron Lett. 1995, 36, 4381. Novak, B. H.; Lash, T. D. J. Org. Chem. 1998, 63, 3998.
18. Lin, Y.; Lash, T. D. Tetrahedron Lett. 1995, 36, 9441.
19. Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998. Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1 1996, 2461.
20. Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998. Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1 1996, 2461.
21. Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998. Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1 1996, 2461.
22. Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715. Lash, T. D.; Novak, B. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 683.
23. Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715. Lash, T. D.; Novak, B. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 683.
24. Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. For tetrabenzoporphyrins, see: Vincente, M. G. H.; Tomé, A. C.; Walter, A.; Cavaleiro, J. A. S. Tetrahedron Lett. 1997, 38, 3639 and references therein.
25. Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. For tetrabenzoporphyrins, see: Vincente, M. G. H.; Tomé, A. C.; Walter, A.; Cavaleiro, J. A. S. Tetrahedron Lett. 1997, 38, 3639 and references therein.
26. Crossley, M. J.; Burn, P. L. J. Chem Soc., Chem. Commun. 1991, 1569. Crossley, M. J.; Prashar, J. K. Tetrahedron Lett. 1997, 38, 6751.
27. Crossley, M. J.; Burn, P. L. J. Chem Soc., Chem. Commun. 1991, 1569. Crossley, M. J.; Prashar, J. K. Tetrahedron Lett. 1997, 38, 6751.
28. Crossley, M. J.; Burn, P. L.; Langford, S. J.; Prashar, J. K. J. Chem. Soc., Chem. Commun. 1995, 1921.
29. Preliminary communication: Chandrasekar, P.; Lash, T. D. Tetrahedron Lett. 1996, 37, 4873.
30. Results presented, in part, at the 210th National Meeting of the American Chemical Society, Chicago, Illinois, August 1995 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 80); the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 6, 1995 (Chandrasekar, P.; Lash, T. D. Trans. Ill. State Acad. Sci. 1995 (Supplement to Volume 88, p 52, Abstract 55)); the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 476).
31. Results presented, in part, at the 210th National Meeting of the American Chemical Society, Chicago, Illinois, August 1995 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 80); the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 6, 1995 (Chandrasekar, P.; Lash, T. D. Trans. Ill. State Acad. Sci. 1995 (Supplement to Volume 88, p 52, Abstract 55)); the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 476).
32. Results presented, in part, at the 210th National Meeting of the American Chemical Society, Chicago, Illinois, August 1995 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 80); the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 6, 1995 (Chandrasekar, P.; Lash, T. D. Trans. Ill. State Acad. Sci. 1995 (Supplement to Volume 88, p 52, Abstract 55)); the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 476).
33. Results presented, in part, at the 210th National Meeting of the American Chemical Society, Chicago, Illinois, August 1995 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 80); the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 6, 1995 (Chandrasekar, P.; Lash, T. D. Trans. Ill. State Acad. Sci. 1995 (Supplement to Volume 88, p 52, Abstract 55)); the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 476).
34. Results presented, in part, at the 210th National Meeting of the American Chemical Society, Chicago, Illinois, August 1995 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 80); the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 6, 1995 (Chandrasekar, P.; Lash, T. D. Trans. Ill. State Acad. Sci. 1995 (Supplement to Volume 88, p 52, Abstract 55)); the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 476).
35. Results presented, in part, at the 210th National Meeting of the American Chemical Society, Chicago, Illinois, August 1995 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 80); the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 6, 1995 (Chandrasekar, P.; Lash, T. D. Trans. Ill. State Acad. Sci. 1995 (Supplement to Volume 88, p 52, Abstract 55)); the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Chandrasekar, P.; Lash, T. D. Book of Abstracts, ORGN 476).
36. Barton, D. H. R.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1985, 1098. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587.
37. Barton, D. H. R.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1985, 1098. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587.
38. (a) Lash, T. D.; Novak, B. H.; Lin, Y. Tetrahedron Lett. 1994, 35, 2493.
39. (b) Lash, T. D.; Wijesinghe, C.; Osuma, A. T.; Patel, J. R. Tetrahedron Lett. 1997, 38, 2031.
40. (a) Ono, N.; Hironaga, H.; Simizu, K.; Ono, K.; Kuwano, K.; Ogawa, T. J. Chem. Soc., Chem. Commun. 1994, 1019.
41. (b) Ono, N.; Hironaga, H.; Ono, K.; Kaneko, S.; Murashima, T.; Ueda, T.; Tsukamura, C.; Ogawa, T. J. Chem. Soc., Perkin Trans. 1 1996, 417.
42. (c) Murashima, T.; Fujita, K.; Ono, K.; Ogawa, T.; Uno, H.; Ono, N. J. Chem. Soc., Perkin Trans. 1 1996, 1403.
43. (d) Murashima, T.; Tamai, R.; Fujita, K.; Uno, H.; Ono, N. Tetrahedron Lett. 1996, 37, 8391. For related studies, see: Jaquinod, L.; Gros, C.; Olmstead, M. M.; Antolovich, M.; Smith, K. M. Chem. Commun. 1996, 1475. Pelkey, E. T.; Chang, L.; Gribble, G. W. Chem. Commun. 1996, 1909. Gros, C. P.; Jaquinod, L.; Khoury, R. G.; Olmstead, M. M.; Smith, K. M. J. Porphyrins Phthalocyanines 1997, 1, 201.
44. (d) Murashima, T.; Tamai, R.; Fujita, K.; Uno, H.; Ono, N. Tetrahedron Lett. 1996, 37, 8391. For related studies, see: Jaquinod, L.; Gros, C.; Olmstead, M. M.; Antolovich, M.; Smith, K. M. Chem. Commun. 1996, 1475. Pelkey, E. T.; Chang, L.; Gribble, G. W. Chem. Commun. 1996, 1909. Gros, C. P.; Jaquinod, L.; Khoury, R. G.; Olmstead, M. M.; Smith, K. M. J. Porphyrins Phthalocyanines 1997, 1, 201.
45. (d) Murashima, T.; Tamai, R.; Fujita, K.; Uno, H.; Ono, N. Tetrahedron Lett. 1996, 37, 8391. For related studies, see: Jaquinod, L.; Gros, C.; Olmstead, M. M.; Antolovich, M.; Smith, K. M. Chem. Commun. 1996, 1475. Pelkey, E. T.; Chang, L.; Gribble, G. W. Chem. Commun. 1996, 1909. Gros, C. P.; Jaquinod, L.; Khoury, R. G.; Olmstead, M. M.; Smith, K. M. J. Porphyrins Phthalocyanines 1997, 1, 201.
46. (d) Murashima, T.; Tamai, R.; Fujita, K.; Uno, H.; Ono, N. Tetrahedron Lett. 1996, 37, 8391. For related studies, see: Jaquinod, L.; Gros, C.; Olmstead, M. M.; Antolovich, M.; Smith, K. M. Chem. Commun. 1996, 1475. Pelkey, E. T.; Chang, L.; Gribble, G. W. Chem. Commun. 1996, 1909. Gros, C. P.; Jaquinod, L.; Khoury, R. G.; Olmstead, M. M.; Smith, K. M. J. Porphyrins Phthalocyanines 1997, 1, 201.
47. (a) Arsenault, G. P.; Bullock, E.; MacDonald, S. F. J. Am. Chem. Soc. 1996, 82, 4384.
48. (b) Cavaleiro, J. A. S.; Rocha Gonsalves, A. M. d'A.; Kenner, G. W.; Smith, K. M. J. Chem. Soc., Perkin Trans. 1 1974, 1771.
49. (c) Lash, T. D.; Catarello, J. J. Tetrahedron 1993, 49, 4159.
50. Jackson, A. H.; Pandey, R. K.; Rao, K. R. N.; Roberts, E. Tetrahedron Lett. 1985, 26, 793.
51. Lash, T. D. Chem.-Eur. J. 1996, 2, 1197.
52. Lash, T. D. J. Porphyrins Phthalocyanines 1997, 1, 29.
53. Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533. Lash, T. D.; Chaney, S. T. Chem.-Eur. J. 1996, 2, 944. Lash, T. D.; Chaney, S. T. Tetrahedron Lett. 1996, 37, 8825. Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Hayes, M. J.; Lash, T. D. Chem.-Eur. J. 1998, 4, 508.
54. Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533. Lash, T. D.; Chaney, S. T. Chem.-Eur. J. 1996, 2, 944. Lash, T. D.; Chaney, S. T. Tetrahedron Lett. 1996, 37, 8825. Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Hayes, M. J.; Lash, T. D. Chem.-Eur. J. 1998, 4, 508.
55. Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533. Lash, T. D.; Chaney, S. T. Chem.-Eur. J. 1996, 2, 944. Lash, T. D.; Chaney, S. T. Tetrahedron Lett. 1996, 37, 8825. Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Hayes, M. J.; Lash, T. D. Chem.-Eur. J. 1998, 4, 508.
56. Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533. Lash, T. D.; Chaney, S. T. Chem.-Eur. J. 1996, 2, 944. Lash, T. D.; Chaney, S. T. Tetrahedron Lett. 1996, 37, 8825. Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Hayes, M. J.; Lash, T. D. Chem.-Eur. J. 1998, 4, 508.
57. Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533. Lash, T. D.; Chaney, S. T. Chem.-Eur. J. 1996, 2, 944. Lash, T. D.; Chaney, S. T. Tetrahedron Lett. 1996, 37, 8825. Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Hayes, M. J.; Lash, T. D. Chem.-Eur. J. 1998, 4, 508.
58. Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533. Lash, T. D.; Chaney, S. T. Chem.-Eur. J. 1996, 2, 944. Lash, T. D.; Chaney, S. T. Tetrahedron Lett. 1996, 37, 8825. Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 839. Hayes, M. J.; Lash, T. D. Chem.-Eur. J. 1998, 4, 508.
59. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2069. Boudif, A.; Momenteau, M. J. Chem. Soc., Perkin Trans. 1 1996, 1235. See also: Sessler, J. L.; Genge, J. W.; Urbach, A.; Sanson, P. Synlett 1996, 187. For an alternative "3 + 1" porphyrin synthesis, see: Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998.
60. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2069. Boudif, A.; Momenteau, M. J. Chem. Soc., Perkin Trans. 1 1996, 1235. See also: Sessler, J. L.; Genge, J. W.; Urbach, A.; Sanson, P. Synlett 1996, 187. For an alternative "3 + 1" porphyrin synthesis, see: Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998.
61. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2069. Boudif, A.; Momenteau, M. J. Chem. Soc., Perkin Trans. 1 1996, 1235. See also: Sessler, J. L.; Genge, J. W.; Urbach, A.; Sanson, P. Synlett 1996, 187. For an alternative "3 + 1" porphyrin synthesis, see: Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998.
62. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2069. Boudif, A.; Momenteau, M. J. Chem. Soc., Perkin Trans. 1 1996, 1235. See also: Sessler, J. L.; Genge, J. W.; Urbach, A.; Sanson, P. Synlett 1996, 187. For an alternative "3 + 1" porphyrin synthesis, see: Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998.
63. Dolphin, D.; Paine, J. B. III; Woodward, R. B. J. Org. Chem. 1976, 41, 2830. For an alternative one-step synthesis of pyrrole-2,5-dicarboxaldehydes, see: Tardieux, C.; Bolze, F.; Gros, C. P.; Guilard, R. Synthesis 1998, 267.
64. Dolphin, D.; Paine, J. B. III; Woodward, R. B. J. Org. Chem. 1976, 41, 2830. For an alternative one-step synthesis of pyrrole-2,5-dicarboxaldehydes, see: Tardieux, C.; Bolze, F.; Gros, C. P.; Guilard, R. Synthesis 1998, 267.
65. Burns, D. H.; Caldwell, T. M.; Burden, M. W. Tetrahedron Lett. 1993, 34, 2883.
66. Jackson, A. H.; Lertwanawatana, W.; Pandey, R. K.; Rao, K. R. N. J. Chem. Soc., Perkin Trans. 1 1989, 374.
67. Lash, T. D.; Chandrasekar, P. J. Am. Chem. Soc. 1996, 118, 8767. See also ref 19b.
68. Results presented, in part, at the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Osuma, A. T.; Lash, T. D. Book of Abstracts, ORGN 478) and the 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Osuma, A. T.; Lash, T. D. Program and Abstracts, Abstract 132).
69. Results presented, in part, at the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Osuma, A. T.; Lash, T. D. Book of Abstracts, ORGN 478) and the 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Osuma, A. T.; Lash, T. D. Program and Abstracts, Abstract 132).
70. Results presented, in part, at the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Osuma, A. T.; Lash, T. D. Book of Abstracts, ORGN 478) and the 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Osuma, A. T.; Lash, T. D. Program and Abstracts, Abstract 132).
71. Results presented, in part, at the 211th National Meeting of the American Chemical Society, New Orleans, Louisiana, March 28, 1996 (Osuma, A. T.; Lash, T. D. Book of Abstracts, ORGN 478) and the 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Osuma, A. T.; Lash, T. D. Program and Abstracts, Abstract 132).
72. lida, H.; Kajiyama, I.; Yamada, K. Nippon Kagaku Kaishi 1972, 137; Chem. Abstr. 1972, 76, 99395m.
73. lida, H.; Kajiyama, I.; Yamada, K. Nippon Kagaku Kaishi 1972, 137; Chem. Abstr. 1972, 76, 99395m.
74. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1979, 59, 183.
75. Lash, T. D.; Bellettini, J. R.; Bastian, J. A.; Couch, K. B. Synthesis 1994, 170. See also: Burns, D. H.; Jabara, C. S.; Burden, M. W. Synth. Commun. 1998, 25, 379.
76. Lash, T. D.; Bellettini, J. R.; Bastian, J. A.; Couch, K. B. Synthesis 1994, 170. See also: Burns, D. H.; Jabara, C. S.; Burden, M. W. Synth. Commun. 1998, 25, 379.
77. Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: 1975; p 798.
78. Adler, A. D.; Longo, F. R.; Kampas, F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 32, 2443.
79. Bullock, E.; Johnson, A. W.; Markham, E.; Shaw, K. B. J. Chem. Soc. 1958, 1430.
80. Lash, T. D. Tetrahedron 1998, 54, 359.
81. Clezy, P. S.; Crowley, R. J.; Hai, T. T. Aust. J. Chem. 1982, 35, 411.
82. Johnson, A. W.; Kay, I. T.; Markham, E.; Price, R.; Shaw, K. B. J. Chem. Soc. 1959, 3416.
83. Clezy, P. S.; Liepa, A. J. Aust. J. Chem. 1970, 23, 2443.