Conjugated macrocycles related to the porphyrins. 12. Oxybenzi- and oxypyriporphyrins: Aromaticity and conjugation in highly modified porphyrinoid structures

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 9076-9088

  Lash, Timothy D ^a   Chaney, Sun T ^a   Richter, Daniel T ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANNULENE DERIVATIVE; BENZENE; CARBON; COPPER; DICHLOROMETHANE; MACROCYCLIC COMPOUND; METALLOPORPHYRIN; NICKEL; PHENANTHRENE; PORPHYRIN DERIVATIVE; SALICYLALDEHYDE; SEMIQUINONE; ZINC;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONJUGATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0031766944     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981872a     Document Type: Article

References (90)

1. Part 10: Hayes, M. J.; Lash, T. D. Chem. Eur. J. 1998, 4, 508. Part 11: Lash, T. D. Chem. Commun. 1998, 1683.
2. Part 10: Hayes, M. J.; Lash, T. D. Chem. Eur. J. 1998, 4, 508. Part 11: Lash, T. D. Chem. Commun. 1998, 1683.
3. Porphyrins and Metalloporphyrins, Smith, K. M., Ed., Elsevier: Amsterdam, 1975.
4. The resilience of the porphyrin macrocycle leads to the survival of metalloporphyrins as biological fossils in organic-rich sediments such as oil shales and petroleum. Baker, E. W.; Palmer, S. E. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1, pp 486-552. Callot, H. J. In The Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, 1991; pp 339-364.
5. The resilience of the porphyrin macrocycle leads to the survival of metalloporphyrins as biological fossils in organic-rich sediments such as oil shales and petroleum. Baker, E. W.; Palmer, S. E. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1, pp 486-552. Callot, H. J. In The Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, 1991; pp 339-364.
6. Badger, G. M.; Elix, J. A.; Lewis, G. E. Aust. J. Chem. 1965, 18, 70. Vogel, E.; Haas, W.; Knipp, B.; Lex, J.; Schmickler, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 406.
7. Badger, G. M.; Elix, J. A.; Lewis, G. E. Aust. J. Chem. 1965, 18, 70. Vogel, E.; Haas, W.; Knipp, B.; Lex, J.; Schmickler, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 406.
8. Lash, T. D. In The Macmillan Encyclopedia of Chemistry; Lagowski, J. J., Ed.; Simon & Schuster Macmillan: New York, 1997, Vol. 3, pp 1239-1245.
9. Lash, T. D.; Chaney, S. T. Tetrahedron Lett. 1996, 37, 8825.
10. Sondheimer, F.; Wolovsky, R. J. Am. Chem. Soc. 1962, 84, 260.
11. Janson, T. R.; Katz, J. J. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 4, pp 1-59. Scheer, H.; Katz, J. J. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975, pp 399-524.
12. Janson, T. R.; Katz, J. J. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 4, pp 1-59. Scheer, H.; Katz, J. J. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975, pp 399-524.
13. Stern, A.; Klebs, G. Ann. Chem. 1932, 500, 91; 1933, 504, 287; 1933, 505, 295.
14. Stern, A.; Klebs, G. Ann. Chem. 1932, 500, 91; 1933, 504, 287; 1933, 505, 295.
15. Stern, A.; Klebs, G. Ann. Chem. 1932, 500, 91; 1933, 504, 287; 1933, 505, 295.
16. Doddrell, D.; Caughey, W. S. J. Am. Chem. Soc. 1972, 94, 2510.
17. Woodward, R. B. Ind. Chim. Belge 1962, 1293. For another viewpoint on porphyrinoid aromaticity, see: Cyranski, M. K.; Krygowski, T. M.; Wisiorowski, M.; Hommes, N. J. R. van E.; Schleyer, P. von R. Angew. Chem., Int. Ed. Engl. 1998, 37, 177.
18. Woodward, R. B. Ind. Chim. Belge 1962, 1293. For another viewpoint on porphyrinoid aromaticity, see: Cyranski, M. K.; Krygowski, T. M.; Wisiorowski, M.; Hommes, N. J. R. van E.; Schleyer, P. von R. Angew. Chem., Int. Ed. Engl. 1998, 37, 177.
19. Storm, C.; Teklu, Y. J. Am. Chem. Soc. 1972, 94, 1745. Abraham, R. J.; Hawkes, G. E.; Smith, K. M. Tetrahedron Lett. 1974, 1483. Irving, C. S.; Lapidot, A. J. Chem. Soc., Chem. Commun., 1977, 184. Goldbeck, R. A.; Bo-Ragner, T.; Wee, A. G. H.; Shu, A. Y. L.; Records, R.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1986, 108, 6449. Crossley, M. J.; Harding, M. M.; Sternhell, S. J. Org. Chem. 1988, 53, 1132. Crossley, M. J.; Harding, M. M.; Sternhell, S, J. Org. Chem. 1992, 57, 1833.
20. Storm, C.; Teklu, Y. J. Am. Chem. Soc. 1972, 94, 1745. Abraham, R. J.; Hawkes, G. E.; Smith, K. M. Tetrahedron Lett. 1974, 1483. Irving, C. S.; Lapidot, A. J. Chem. Soc., Chem. Commun., 1977, 184. Goldbeck, R. A.; Bo-Ragner, T.; Wee, A. G. H.; Shu, A. Y. L.; Records, R.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1986, 108, 6449. Crossley, M. J.; Harding, M. M.; Sternhell, S. J. Org. Chem. 1988, 53, 1132. Crossley, M. J.; Harding, M. M.; Sternhell, S, J. Org. Chem. 1992, 57, 1833.
21. Storm, C.; Teklu, Y. J. Am. Chem. Soc. 1972, 94, 1745. Abraham, R. J.; Hawkes, G. E.; Smith, K. M. Tetrahedron Lett. 1974, 1483. Irving, C. S.; Lapidot, A. J. Chem. Soc., Chem. Commun., 1977, 184. Goldbeck, R. A.; Bo-Ragner, T.; Wee, A. G. H.; Shu, A. Y. L.; Records, R.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1986, 108, 6449. Crossley, M. J.; Harding, M. M.; Sternhell, S. J. Org. Chem. 1988, 53, 1132. Crossley, M. J.; Harding, M. M.; Sternhell, S, J. Org. Chem. 1992, 57, 1833.
22. Storm, C.; Teklu, Y. J. Am. Chem. Soc. 1972, 94, 1745. Abraham, R. J.; Hawkes, G. E.; Smith, K. M. Tetrahedron Lett. 1974, 1483. Irving, C. S.; Lapidot, A. J. Chem. Soc., Chem. Commun., 1977, 184. Goldbeck, R. A.; Bo-Ragner, T.; Wee, A. G. H.; Shu, A. Y. L.; Records, R.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1986, 108, 6449. Crossley, M. J.; Harding, M. M.; Sternhell, S. J. Org. Chem. 1988, 53, 1132. Crossley, M. J.; Harding, M. M.; Sternhell, S, J. Org. Chem. 1992, 57, 1833.
23. Storm, C.; Teklu, Y. J. Am. Chem. Soc. 1972, 94, 1745. Abraham, R. J.; Hawkes, G. E.; Smith, K. M. Tetrahedron Lett. 1974, 1483. Irving, C. S.; Lapidot, A. J. Chem. Soc., Chem. Commun., 1977, 184. Goldbeck, R. A.; Bo-Ragner, T.; Wee, A. G. H.; Shu, A. Y. L.; Records, R.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1986, 108, 6449. Crossley, M. J.; Harding, M. M.; Sternhell, S. J. Org. Chem. 1988, 53, 1132. Crossley, M. J.; Harding, M. M.; Sternhell, S, J. Org. Chem. 1992, 57, 1833.
24. Storm, C.; Teklu, Y. J. Am. Chem. Soc. 1972, 94, 1745. Abraham, R. J.; Hawkes, G. E.; Smith, K. M. Tetrahedron Lett. 1974, 1483. Irving, C. S.; Lapidot, A. J. Chem. Soc., Chem. Commun., 1977, 184. Goldbeck, R. A.; Bo-Ragner, T.; Wee, A. G. H.; Shu, A. Y. L.; Records, R.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1986, 108, 6449. Crossley, M. J.; Harding, M. M.; Sternhell, S. J. Org. Chem. 1988, 53, 1132. Crossley, M. J.; Harding, M. M.; Sternhell, S, J. Org. Chem. 1992, 57, 1833.
25. Crossley, M. J.; Harding, M. M.; Sternhell, S. J. Am. Chem. Soc. 1992, 114, 3266.
26. Hoard, J. L. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975; pp 317-380.
27. E.g., Crossley, M. J.; Burn, P. L.; Chew, S. S.; Cuttance, F. B.; Newsom, I. A. J. Chem. Soc., Chem. Commun. 1991, 1564.
28. Vogel, E.; Kocher, M.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. Engl. 1986, 25, 257.
29. Vogel, E. J. Heterocycl. Chem. 1996, 33, 1461.
30. Chmielewski, P. J.; Latos-Grazynski, L.; Rachlewicz, K.; Glowiak, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 779; Furuta, H.; Asano, T.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 767.
31. Chmielewski, P. J.; Latos-Grazynski, L.; Rachlewicz, K.; Glowiak, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 779; Furuta, H.; Asano, T.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 767.
32. Bauer, V. J.; Clive, D. R.; Dolphin, D.; Paine III, J. B.; Harris, F. L.; King, M. M.; Loder, J.; Wang, S.-W. C.; Woodward, R. B. J. Am. Chem. Soc. 1983, 105, 6429. Broadhurst, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc., Perkin Trans. 1 1972, 1124. Sessler, J. L.; Burrell, A. K. Top. Curr. Chem. 1991, 161, 177-273. Ayub, J.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
33. Bauer, V. J.; Clive, D. R.; Dolphin, D.; Paine III, J. B.; Harris, F. L.; King, M. M.; Loder, J.; Wang, S.-W. C.; Woodward, R. B. J. Am. Chem. Soc. 1983, 105, 6429. Broadhurst, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc., Perkin Trans. 1 1972, 1124. Sessler, J. L.; Burrell, A. K. Top. Curr. Chem. 1991, 161, 177-273. Ayub, J.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
34. Bauer, V. J.; Clive, D. R.; Dolphin, D.; Paine III, J. B.; Harris, F. L.; King, M. M.; Loder, J.; Wang, S.-W. C.; Woodward, R. B. J. Am. Chem. Soc. 1983, 105, 6429. Broadhurst, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc., Perkin Trans. 1 1972, 1124. Sessler, J. L.; Burrell, A. K. Top. Curr. Chem. 1991, 161, 177-273. Ayub, J.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
35. Bauer, V. J.; Clive, D. R.; Dolphin, D.; Paine III, J. B.; Harris, F. L.; King, M. M.; Loder, J.; Wang, S.-W. C.; Woodward, R. B. J. Am. Chem. Soc. 1983, 105, 6429. Broadhurst, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc., Perkin Trans. 1 1972, 1124. Sessler, J. L.; Burrell, A. K. Top. Curr. Chem. 1991, 161, 177-273. Ayub, J.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
36. Berger, R. A.; LeGoff, E. Tetrahedron Lett. 1978, 4225. Franck, B.; Nonn, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1795.
37. Berger, R. A.; LeGoff, E. Tetrahedron Lett. 1978, 4225. Franck, B.; Nonn, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1795.
38. Lin, Y.; Lash, T. D. Tetrahedron Lett. 1995, 36, 9441.
39. Chandrasekar, P.; Lash, T. D. Tetrahedron Lett. 1996, 37, 4873.
40. Lash, T. D.; Chandrasekar, P.; Osuma, A. T.; Chaney, S. T.; Spence, J. D. J. Org. Chem., in press.
41. Lash, T. D.; Chaney, S. T. Chem. Eur. J. 1996, 2, 944.
42. Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 840.
43. Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839.
44. Lash, T. D.; Wijesinghe, C.; Osuma, A. T.; Patel, J. R. Tetrahedron Lett. 1997, 38, 2031.
45. Lash, T. D. J. Porphyrins Phthalocyanines 1997, 1, 29.
46. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2069; Boudif, A.; Momenteau, M. J. Chem. Soc., Perkin Trans. 1 1996, 1235.
47. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2069; Boudif, A.; Momenteau, M. J. Chem. Soc., Perkin Trans. 1 1996, 1235.
48. Berlin, K.; Steinbeck, C.; Breitmaier, E. Synthesis 1996, 336. Berlin, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1820.
49. Berlin, K.; Steinbeck, C.; Breitmaier, E. Synthesis 1996, 336. Berlin, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1820.
50. Lash, T. D. Chem. Eur. J. 1996, 2, 1197.
51. Broadhurst, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc. (C) 1971, 3681. Johnson, A. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975; pp 729-754.
52. Broadhurst, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc. (C) 1971, 3681. Johnson, A. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975; pp 729-754.
53. Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246. See also: Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219.
54. Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246. See also: Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219.
55. Preliminary communication: Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533.
56. Results on the synthesis and spectroscopic properties of oxybenziporphyrins were presented, in part, at the 210th National ACS Meeting, Chicago, IL, August 1995 (Abstract: Lash, T. D.; Lin, Y. Book of Abstracts, ORGN 179); 211th National ACS Meeting, New Orleans, Louisiana, March 1996 (Abstract: Lash, T. D.; Chaney, S. T. Book of Abstracts ORGN 475); Symposium on Advances in Natural Products Synthesis, 28th Central Regional ACS Meeting, Dayton, OH, June 1996 (Abstract: Lash, T. D. Program and Abstracts Abstract No. 201).
57. Results on the synthesis and spectroscopic properties of oxybenziporphyrins were presented, in part, at the 210th National ACS Meeting, Chicago, IL, August 1995 (Abstract: Lash, T. D.; Lin, Y. Book of Abstracts, ORGN 179); 211th National ACS Meeting, New Orleans, Louisiana, March 1996 (Abstract: Lash, T. D.; Chaney, S. T. Book of Abstracts ORGN 475); Symposium on Advances in Natural Products Synthesis, 28th Central Regional ACS Meeting, Dayton, OH, June 1996 (Abstract: Lash, T. D. Program and Abstracts Abstract No. 201).
58. Results on the synthesis and spectroscopic properties of oxybenziporphyrins were presented, in part, at the 210th National ACS Meeting, Chicago, IL, August 1995 (Abstract: Lash, T. D.; Lin, Y. Book of Abstracts, ORGN 179); 211th National ACS Meeting, New Orleans, Louisiana, March 1996 (Abstract: Lash, T. D.; Chaney, S. T. Book of Abstracts ORGN 475); Symposium on Advances in Natural Products Synthesis, 28th Central Regional ACS Meeting, Dayton, OH, June 1996 (Abstract: Lash, T. D. Program and Abstracts Abstract No. 201).
59. Results on the oxypyriporphyrins were presented, in part, at the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 1995 (Abstract: Chaney, S. T.; Lash, T. D. Transactions of the Illinois State Academy of Science 1995, Supplement to Vol. 88, p 51, Abstract No. 53); 211th National ACS Meeting, New Orleans, Louisiana, March 1996 (Abstract: Chaney, S. T.; Lash, T. D. Book of Abstracts ORGN 477); 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 135); 28th Central Regional ACS Meeting, Dayton, Ohio, June 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 191). A popularized account of these studies also appeared in the September 1, 1997 issue of Chemical & Engineering News: Freemantle, M. Porphyrin Route Revival: Aromatic Porphyrinoids Synthesized by '3 + 1′ Condensation. Chem. Eng. News 1997, 75 (35), 31-33.
60. Results on the oxypyriporphyrins were presented, in part, at the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 1995 (Abstract: Chaney, S. T.; Lash, T. D. Transactions of the Illinois State Academy of Science 1995, Supplement to Vol. 88, p 51, Abstract No. 53); 211th National ACS Meeting, New Orleans, Louisiana, March 1996 (Abstract: Chaney, S. T.; Lash, T. D. Book of Abstracts ORGN 477); 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 135); 28th Central Regional ACS Meeting, Dayton, Ohio, June 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 191). A popularized account of these studies also appeared in the September 1, 1997 issue of Chemical & Engineering News: Freemantle, M. Porphyrin Route Revival: Aromatic Porphyrinoids Synthesized by '3 + 1′ Condensation. Chem. Eng. News 1997, 75 (35), 31-33.
61. Results on the oxypyriporphyrins were presented, in part, at the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 1995 (Abstract: Chaney, S. T.; Lash, T. D. Transactions of the Illinois State Academy of Science 1995, Supplement to Vol. 88, p 51, Abstract No. 53); 211th National ACS Meeting, New Orleans, Louisiana, March 1996 (Abstract: Chaney, S. T.; Lash, T. D. Book of Abstracts ORGN 477); 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 135); 28th Central Regional ACS Meeting, Dayton, Ohio, June 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 191). A popularized account of these studies also appeared in the September 1, 1997 issue of Chemical & Engineering News: Freemantle, M. Porphyrin Route Revival: Aromatic Porphyrinoids Synthesized by '3 + 1′ Condensation. Chem. Eng. News 1997, 75 (35), 31-33.
62. Results on the oxypyriporphyrins were presented, in part, at the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 1995 (Abstract: Chaney, S. T.; Lash, T. D. Transactions of the Illinois State Academy of Science 1995, Supplement to Vol. 88, p 51, Abstract No. 53); 211th National ACS Meeting, New Orleans, Louisiana, March 1996 (Abstract: Chaney, S. T.; Lash, T. D. Book of Abstracts ORGN 477); 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 135); 28th Central Regional ACS Meeting, Dayton, Ohio, June 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 191). A popularized account of these studies also appeared in the September 1, 1997 issue of Chemical & Engineering News: Freemantle, M. Porphyrin Route Revival: Aromatic Porphyrinoids Synthesized by '3 + 1′ Condensation. Chem. Eng. News 1997, 75 (35), 31-33.
63. Results on the oxypyriporphyrins were presented, in part, at the 88th Annual Meeting of the Illinois State Academy of Science, Eastern Illinois University, Charleston, Illinois, October 1995 (Abstract: Chaney, S. T.; Lash, T. D. Transactions of the Illinois State Academy of Science 1995, Supplement to Vol. 88, p 51, Abstract No. 53); 211th National ACS Meeting, New Orleans, Louisiana, March 1996 (Abstract: Chaney, S. T.; Lash, T. D. Book of Abstracts ORGN 477); 29th Great Lakes Regional American Chemical Society Meeting, Normal, Illinois, May 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 135); 28th Central Regional ACS Meeting, Dayton, Ohio, June 1996 (Abstract: Chaney, S. T.; Lash, T. D. Program and Abstracts Abstract No. 191). A popularized account of these studies also appeared in the September 1, 1997 issue of Chemical & Engineering News: Freemantle, M. Porphyrin Route Revival: Aromatic Porphyrinoids Synthesized by '3 + 1′ Condensation. Chem. Eng. News 1997, 75 (35), 31-33.
64. Porphyrinoid chromophores with strong absorptions at longer wavelengths (>700 nm) have attracted considerable attention in recent years because of their intrinsic value in the development of novel optical materials with potential applications in optical recording technology, etc., and as superior photosensitizers for singlet oxygen formation in photodynamic therapy. See: Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19. Milgrom, L. R.; MacRobert, S. Chem. Br. 1998, 34 (35), 45.
65. Porphyrinoid chromophores with strong absorptions at longer wavelengths (>700 nm) have attracted considerable attention in recent years because of their intrinsic value in the development of novel optical materials with potential applications in optical recording technology, etc., and as superior photosensitizers for singlet oxygen formation in photodynamic therapy. See: Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19. Milgrom, L. R.; MacRobert, S. Chem. Br. 1998, 34 (35), 45.
66. Porphyrinoid chromophores with strong absorptions at longer wavelengths (>700 nm) have attracted considerable attention in recent years because of their intrinsic value in the development of novel optical materials with potential applications in optical recording technology, etc., and as superior photosensitizers for singlet oxygen formation in photodynamic therapy. See: Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19. Milgrom, L. R.; MacRobert, S. Chem. Br. 1998, 34 (35), 45.
67. Sessler, J. L.; Johnson, M. R.; Lynch, V. J. Org. Chem. 1987, 52, 4394. Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998
68. Sessler, J. L.; Johnson, M. R.; Lynch, V. J. Org. Chem. 1987, 52, 4394. Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998
69. Mono-and dibenzoporphyrins: (a) Lash, T. D. Energy Fuels 1993, 7, 166. (b) Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. (c) Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. (d) Clezy, P. S.; Leung, C. W. F. Aust. J. Chem. 1993, 46, 6, 1705. (e) Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1996, 2461. See also, May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820. Lash, T. D. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: 1995; Vol. 1, pp 19-69.
70. Mono-and dibenzoporphyrins: (a) Lash, T. D. Energy Fuels 1993, 7, 166. (b) Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. (c) Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. (d) Clezy, P. S.; Leung, C. W. F. Aust. J. Chem. 1993, 46, 6, 1705. (e) Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1996, 2461. See also, May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820. Lash, T. D. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: 1995; Vol. 1, pp 19-69.
71. Mono-and dibenzoporphyrins: (a) Lash, T. D. Energy Fuels 1993, 7, 166. (b) Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. (c) Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. (d) Clezy, P. S.; Leung, C. W. F. Aust. J. Chem. 1993, 46, 6, 1705. (e) Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1996, 2461. See also, May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820. Lash, T. D. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: 1995; Vol. 1, pp 19-69.
72. Mono-and dibenzoporphyrins: (a) Lash, T. D. Energy Fuels 1993, 7, 166. (b) Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. (c) Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. (d) Clezy, P. S.; Leung, C. W. F. Aust. J. Chem. 1993, 46, 6, 1705. (e) Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1996, 2461. See also, May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820. Lash, T. D. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: 1995; Vol. 1, pp 19-69.
73. Mono-and dibenzoporphyrins: (a) Lash, T. D. Energy Fuels 1993, 7, 166. (b) Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. (c) Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. (d) Clezy, P. S.; Leung, C. W. F. Aust. J. Chem. 1993, 46, 6, 1705. (e) Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1996, 2461. See also, May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820. Lash, T. D. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: 1995; Vol. 1, pp 19-69.
74. Mono-and dibenzoporphyrins: (a) Lash, T. D. Energy Fuels 1993, 7, 166. (b) Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. (c) Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. (d) Clezy, P. S.; Leung, C. W. F. Aust. J. Chem. 1993, 46, 6, 1705. (e) Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1996, 2461. See also, May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820. Lash, T. D. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: 1995; Vol. 1, pp 19-69.
75. Mono-and dibenzoporphyrins: (a) Lash, T. D. Energy Fuels 1993, 7, 166. (b) Clezy, P. S.; Fookes, C. J. R.; Mirza, A. H. Aust. J. Chem. 1977, 30, 1337. (c) Clezy, P. S.; Mirza, A. H. Aust. J. Chem. 1982, 35, 197. (d) Clezy, P. S.; Leung, C. W. F. Aust. J. Chem. 1993, 46, 6, 1705. (e) Bonnett, R.; McManus, K. A. J. Chem. Soc., Perkin Trans. 1996, 2461. See also, May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820. Lash, T. D. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: 1995; Vol. 1, pp 19-69.
76. Naphthoporphyrins: Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715. Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59. Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. Kopranenkov, V. N.; Vorotnikov, A. M.; Dashkevich, S. N.; Luk'yanets, E. A. J. Gen, Chem. USSR 1985, 55, 803. Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
77. Naphthoporphyrins: Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715. Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59. Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. Kopranenkov, V. N.; Vorotnikov, A. M.; Dashkevich, S. N.; Luk'yanets, E. A. J. Gen, Chem. USSR 1985, 55, 803. Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
78. Naphthoporphyrins: Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715. Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59. Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. Kopranenkov, V. N.; Vorotnikov, A. M.; Dashkevich, S. N.; Luk'yanets, E. A. J. Gen, Chem. USSR 1985, 55, 803. Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
79. Naphthoporphyrins: Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715. Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59. Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. Kopranenkov, V. N.; Vorotnikov, A. M.; Dashkevich, S. N.; Luk'yanets, E. A. J. Gen, Chem. USSR 1985, 55, 803. Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
80. Naphthoporphyrins: Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715. Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59. Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. Kopranenkov, V. N.; Vorotnikov, A. M.; Dashkevich, S. N.; Luk'yanets, E. A. J. Gen, Chem. USSR 1985, 55, 803. Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
81. Naphthoporphyrins: Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715. Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59. Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. Kopranenkov, V. N.; Vorotnikov, A. M.; Dashkevich, S. N.; Luk'yanets, E. A. J. Gen, Chem. USSR 1985, 55, 803. Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199.
82. Phenanthroporphyrins: Lash, T. D.; Novak, B. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 4, 683. Lash, T. D.; Novak, B. H. Tetrahedron Lett. 1995, 36, 4381. Novak, B. H.; Lash, T. D. J. Org. Chem. 1998, 63, 3998.
83. Phenanthroporphyrins: Lash, T. D.; Novak, B. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 4, 683. Lash, T. D.; Novak, B. H. Tetrahedron Lett. 1995, 36, 4381. Novak, B. H.; Lash, T. D. J. Org. Chem. 1998, 63, 3998.
84. Phenanthroporphyrins: Lash, T. D.; Novak, B. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 4, 683. Lash, T. D.; Novak, B. H. Tetrahedron Lett. 1995, 36, 4381. Novak, B. H.; Lash, T. D. J. Org. Chem. 1998, 63, 3998.
85. Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: New York, 1975; pp 871-889.
86. Lash, T. D.; Chandrasekar, P. J. Am. Chem. Soc. 1996, 118, 8767.
87. Jackson, A. H.; Lertwanawatana, W.; Pandey, R. K.; Rao, K. R. N. J. Chem. Soc., Perkin Trans, 1 1989, 374.
88. Jackson, A. H.; Kenner, G. W.; Smith, K. M. J. Chem. Soc. (C) 1971, 502.
89. For further commentary, see ref 25.
90. 2) using a crude preparation of diformylpyridine 32 and presumably for this reason isolated the product in relatively low yield (23%).