Formation of a meso-Tetraphenylsecochlorin and a Homoporphyrin with a Twist

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2094-2098

  Brückner, Christian ^a,b   Rettig, Steven J ^a   Dolphin, David ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037968998     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971156t     Document Type: Article

References (47)

1. For reviews on synthetic aspects of synthetic and naturally occurring chlorins see: (a) Scheer, H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 1. (b) Scheer, H.; Inhoffen, H. H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 2. (c) Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73-126. Chlorophylls; Scheer, H., Ed.; CRC: Boca Raton, 1991. (e) Montforts, F.-P.; Gerlach, B.; Höper, F. Chem. Rev. 1994, 94, 327-347.
2. For reviews on synthetic aspects of synthetic and naturally occurring chlorins see: (a) Scheer, H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 1. (b) Scheer, H.; Inhoffen, H. H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 2. (c) Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73-126. Chlorophylls; Scheer, H., Ed.; CRC: Boca Raton, 1991. (e) Montforts, F.-P.; Gerlach, B.; Höper, F. Chem. Rev. 1994, 94, 327-347.
3. For reviews on synthetic aspects of synthetic and naturally occurring chlorins see: (a) Scheer, H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 1. (b) Scheer, H.; Inhoffen, H. H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 2. (c) Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73-126. Chlorophylls; Scheer, H., Ed.; CRC: Boca Raton, 1991. (e) Montforts, F.-P.; Gerlach, B.; Höper, F. Chem. Rev. 1994, 94, 327-347.
4. For reviews on synthetic aspects of synthetic and naturally occurring chlorins see: (a) Scheer, H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 1. (b) Scheer, H.; Inhoffen, H. H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 2. (c) Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73-126. Chlorophylls; Scheer, H., Ed.; CRC: Boca Raton, 1991. (e) Montforts, F.-P.; Gerlach, B.; Höper, F. Chem. Rev. 1994, 94, 327-347.
5. For reviews on synthetic aspects of synthetic and naturally occurring chlorins see: (a) Scheer, H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 1. (b) Scheer, H.; Inhoffen, H. H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, Chapter 2. (c) Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73-126. Chlorophylls; Scheer, H., Ed.; CRC: Boca Raton, 1991. (e) Montforts, F.-P.; Gerlach, B.; Höper, F. Chem. Rev. 1994, 94, 327-347.
6. (a) Photodynamic Theory: Basic Principles and Clinical Applications; Henderson, B. W., Dougherty, T. J., Eds.; Marcel Dekker: New York, 1992.
7. For overview articles see: (b) Brown, S. B.; Truscott, T. G. Chem. Br. 1993, 11, 955-958. (c) Dolphin, D. Can. J. Chem. 1994, 72, 1005-1013. (d) Bonnett, R. Chem. Soc. Rev. 1995, 19-33. (e) Sternberg, E.; Dolphin, D. Curr. Med. Chem. 1996, 3, 293-324.
8. For overview articles see: (b) Brown, S. B.; Truscott, T. G. Chem. Br. 1993, 11, 955-958. (c) Dolphin, D. Can. J. Chem. 1994, 72, 1005-1013. (d) Bonnett, R. Chem. Soc. Rev. 1995, 19-33. (e) Sternberg, E.; Dolphin, D. Curr. Med. Chem. 1996, 3, 293-324.
9. For overview articles see: (b) Brown, S. B.; Truscott, T. G. Chem. Br. 1993, 11, 955-958. (c) Dolphin, D. Can. J. Chem. 1994, 72, 1005-1013. (d) Bonnett, R. Chem. Soc. Rev. 1995, 19-33. (e) Sternberg, E.; Dolphin, D. Curr. Med. Chem. 1996, 3, 293-324.
10. For overview articles see: (b) Brown, S. B.; Truscott, T. G. Chem. Br. 1993, 11, 955-958. (c) Dolphin, D. Can. J. Chem. 1994, 72, 1005-1013. (d) Bonnett, R. Chem. Soc. Rev. 1995, 19-33. (e) Sternberg, E.; Dolphin, D. Curr. Med. Chem. 1996, 3, 293-324.
11. The nomenclature of porphyrinoid systems with cleaved β,β′-bonds as well as incorporation of six-membered rings is variable; see refs 5, 6, and 8. We adopted the nomenclature suggested in ref 8.
12. Nonaromatic porphyrin analogues incorporating six-membered rings: (a) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219-220. (b) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246-1247. Aromatic systems: (c) Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun. 1984, 920-922. Reference 8. (e) Lash, T. D. Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535. (f) Lash, T. D.; Chang, S. T. Tetrahedron Lett. 1996, 49, 8825-8828. (g) Lash, T. D.; Chang, S. T. Chem.-Eur. J. 1996, 8, 944-948.
13. Nonaromatic porphyrin analogues incorporating six-membered rings: (a) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219-220. (b) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246-1247. Aromatic systems: (c) Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun. 1984, 920-922. Reference 8. (e) Lash, T. D. Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535. (f) Lash, T. D.; Chang, S. T. Tetrahedron Lett. 1996, 49, 8825-8828. (g) Lash, T. D.; Chang, S. T. Chem.-Eur. J. 1996, 8, 944-948.
14. Nonaromatic porphyrin analogues incorporating six-membered rings: (a) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219-220. (b) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246-1247. Aromatic systems: (c) Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun. 1984, 920-922. Reference 8. (e) Lash, T. D. Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535. (f) Lash, T. D.; Chang, S. T. Tetrahedron Lett. 1996, 49, 8825-8828. (g) Lash, T. D.; Chang, S. T. Chem.-Eur. J. 1996, 8, 944-948.
15. Nonaromatic porphyrin analogues incorporating six-membered rings: (a) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219-220. (b) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246-1247. Aromatic systems: (c) Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun. 1984, 920-922. Reference 8. (e) Lash, T. D. Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535. (f) Lash, T. D.; Chang, S. T. Tetrahedron Lett. 1996, 49, 8825-8828. (g) Lash, T. D.; Chang, S. T. Chem.-Eur. J. 1996, 8, 944-948.
16. Nonaromatic porphyrin analogues incorporating six-membered rings: (a) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219-220. (b) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246-1247. Aromatic systems: (c) Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun. 1984, 920-922. Reference 8. (e) Lash, T. D. Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535. (f) Lash, T. D.; Chang, S. T. Tetrahedron Lett. 1996, 49, 8825-8828. (g) Lash, T. D.; Chang, S. T. Chem.-Eur. J. 1996, 8, 944-948.
17. Nonaromatic porphyrin analogues incorporating six-membered rings: (a) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219-220. (b) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246-1247. Aromatic systems: (c) Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun. 1984, 920-922. Reference 8. (e) Lash, T. D. Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535. (f) Lash, T. D.; Chang, S. T. Tetrahedron Lett. 1996, 49, 8825-8828. (g) Lash, T. D.; Chang, S. T. Chem.-Eur. J. 1996, 8, 944-948.
18. Nonaromatic porphyrin analogues incorporating six-membered rings: (a) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 219-220. (b) Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246-1247. Aromatic systems: (c) Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun. 1984, 920-922. Reference 8. (e) Lash, T. D. Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535. (f) Lash, T. D.; Chang, S. T. Tetrahedron Lett. 1996, 49, 8825-8828. (g) Lash, T. D.; Chang, S. T. Chem.-Eur. J. 1996, 8, 944-948.
19. (a) Flitsch, W. Pure. Appl. Chem. 1986, 58, 153-160.
20. (b) Bohusch, M.; Flitsch, W.; Kneip, H. G. Liebigs Ann. Chem. 1991, 67-70.
21. Chang, C. K.; Wu, W.; Chern, S.-S.; Peng, S.-M. Angew. Chem., Int. Ed. Engl. 1992, 31, 70-72. Interestingly, this rearrangement was first reported in 1969 by Johnson and co-workers but was misinterpreted: Grigg, R.; Johnson, A. W.; Shelton, K. W. J. Chem. Soc. C 1969, 655-666. Hamilton, A.; Johnson, A. W. J. Chem. Soc. C 1971, 3879-3882.
22. Chang, C. K.; Wu, W.; Chern, S.-S.; Peng, S.-M. Angew. Chem., Int. Ed. Engl. 1992, 31, 70-72. Interestingly, this rearrangement was first reported in 1969 by Johnson and co-workers but was misinterpreted: Grigg, R.; Johnson, A. W.; Shelton, K. W. J. Chem. Soc. C 1969, 655-666. Hamilton, A.; Johnson, A. W. J. Chem. Soc. C 1971, 3879-3882.
23. Interestingly, this rearrangement was first reported in 1969 by Johnson and co-workers but was misinterpreted: Grigg, R.; Johnson, A. W.; Shelton, K. W. J. Chem. Soc. C 1969, 655-666. Hamilton, A.; Johnson, A. W. J. Chem. Soc. C 1971, 3879-3882.
24. (a) Mani, S. N.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, A. G. M.; Hoffman, B. M. J. Chem. Soc., Chem. Commun. 1994, 1943-1944.
25. (b) Garrido Montalban, A.; Lange, S. J.; Beall, L. S.; Mani, N. S.; Williams, D. J.; White, A. J. P.; Barrett, A. G. M.; Hoffman, B. M. J. Org. Chem. 1997, 62, 9283-9289.
26. (a) Adams, K. R.; Bonnett, R.; Burke, P. J.; Salgado, A.; Vallés, M. A. J. Chem. Soc., Chem. Commun. 1993, 1860-1861.
27. (b) Adams, K. R.; Bonnett, R.; Burke, P. J.; Salgado, A.; Asunción Vallés, M. J. Chem. Soc. Perkin Trans. 1 1997, 1769-1772.
28. (a) Ravikanth, M.; Chandrashekar, T. K. Struct. Bond (Berlin) 1995, 82, 107-188.
29. For the seminal reviews of the field see: (b) Scheidt, W. R. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 3; Chapter 10. (c) Scheidt, W. R.; Lee, Y. L. Struct. Bond. (Berlin) 1987, 64, 1-70.
30. For the seminal reviews of the field see: (b) Scheidt, W. R. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 3; Capter 10. (c) Scheidt, W. R.; Lee, Y. L. Struct. Bond. (Berlin) 1987, 64, 1-70.
31. (a) Brückner, C.; Dolphin, D. Tetrahedron Lett. 1995, 36, 3295-3298.
32. (b) Brückner, C.; Dolphin, D. Tetrahedron Lett. 1995, 36, 9425-9428.
33. (a) Fisher, H.; Eckoldt, H. Liebigs Ann. Chem. 1940, 543, 138-162.
34. (b) Fishcher, H.; Preiffer, H. Liebigs Ann. Chem. 1944, 556, 131-153.
35. (c) Chang, C. G.; Sotiriou, C.; Weishih, W. J. Chem. Soc., Chem. Commun. 1986, 1213-1215.
36. (d) Bonnett, R.; Nizhnik, A. N.; Berenbaum, M. C. J. Chem. Soc., Chem. Commun. 1989, 1822-1823.
37. (e) Pandey, K. R.; Shiau, F. Y.; Isaac, M.; Ramaprasad, S.; Dougherty, T. J.; Smith, K. M. Tetrahederon Lett. 1992, 33, 7815-7818.
38. (f) Admas, K. R.; Berenbaum, M. C.; Bonnett, R.; Nizhnik, A. N.; Salgado, A.; Asunción Vallés, M. J. Chem. Soc. Perkin Trans. 1 1992, 1465-1470.
39. Buchler, J. M. In The Porphyrins; Dolphin, D.; Ed.; Academic Press: New York, 1978; Vol. 1; Chapter 10.
40. eq values, tables of bond lengths, angles and torsion angles, and tables of least-squares planes are available upon request from the Director of the Cambridge Crystallographic Data Center, University Chemical Laboratory, Lensfield Road, GB-Cambridge CB2 1EW, U.K., on quoting the full journal citation.
41. Byrn, M. P.; Curtis, C. J.; Hsiou, Y.; Khan, S. I.; Sawin, P. A.; Tendick, S. K.; Terzis, A.; Strouse, C. E. J. Am. Chem. Soc. 1993, 115, 9480-9497.
42. Crystals of pure 9 of high quality could also be grown; however, due to the high quality of the structure analysis of 11 and the isomorphous appearance of both crystals, their study by X-ray diffraction was not persued.
43. (a) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: Berlin, 1983.
44. (b) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983.
45. Atoms defining plane (mean deviation, ψ2)-1: N(1), N(2), N(3), N(4) (0.0350, 913). 2: N(2), C(6), C(7), C(8), C(9) (0.0176, 174); 2: N(3), C(11), C(12), N(13), N(14) (0.0109, 74.1). 3: N(4), C(16), C(17), C(18), C(19) (0.0135, 103.4). Dihedral angle (deg) between planes: 1/2 (156.3); 1/3 (21.6); 1/4 (24.2); 1/5 (84.8); 2/3 (152.8); 2/4 (132.9); 2/5 (73.9); 3/4 (30.8); 3/5 (98.8); 4/5 (68.1).
46. For (octaethylporphyrinato)Ni(II). Collins, D. M.; Buchler, J. W.; Schmidt, W. R. J. Am. Chem. Soc. 1972, 94, 6689-6698.
47. teXsan: Structure Analysis Package; Molecular Structure Corporation: The Woodlands, TX, 1995.