Thermolysis of vic-dihydroxybacteriochlorins: A new approach for the synthesis of chlorin-chlorin and chlorin-porphyrin dimers

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1193-1196

  Kozyrev, Andrei N ^a   Zheng, Gang ^a   Shibata, Masayuki ^a   Alderfer, James L ^a   Dougherty, Thomas J ^a   Pandey, Ravindra K ^a  

^a ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIN; PORPHYRIN;

ARTICLE; CHEMISTRY; DIMERIZATION; HYDROLYSIS; TEMPERATURE;

DIMERIZATION; HYDROLYSIS; PORPHYRINS; TEMPERATURE;

EID: 0033592495     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990150i     Document Type: Article

References (26)

1. (a) The Photosynthetic Reaction Center; Norris, J. R., Deisenhofer, J., Eds.; Academic Press: San Diego, 1993.
2. (b) Wasielewski, M. R. Chem. Rev. 1992, 92, 435 and references therein.
3. (a) Jaquinod, L.; Nurco, D. J.; Medforth, C. J.; Pandey, R. K.; Forsyth, T. P.; Olmstead, M. M. and Smith, K. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1013.
4. (b) Jaquinod, L.; Senge, M. O.; Pandey, R. K.; Forsyth, T. P. and Smith, K. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1840.
5. (c) Kozyrev, A. N.; Alderfer, J. L.; Srikrishnan, T.; Pandey, R. K. J. Chem. Soc., Perkin Trans. 1 1998, 837.
6. (d) Zheng, G.; Alderfer, J. L.; Senge, M. O.; Shibata, M.; Dougherty, T. J. and Pandey, R. K. J. Org. Chem. 1998, 6434.
7. (e) Johnson, C. K.; Dolphin, D. Tetrahedron Lett. 1998, 39, 4753.
8. (f) Krattinger, B.; Nurco, D. J.; Smith, K. M. Chem. Commun. 1998, 757.
9. (a) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936.
10. (b) Knapp, S.; Vasudevan, J.; Emge, T. J.; Arisen, B. H.; Potenza, J. A.; Schugar, H. J. Angew. Chem. Int. Ed. 1998, 37, 2368.
11. (c) Paolesse, R.; Pandey, R. K.; Forsyth, T. P.; Jaquinod, L.; Gerzevske, K. R.; Nurco, D. L.; Senge, M. O.; Licoccia, S.; Boschi, T. and Smith, K. M. J. Am. Chem. Soc. 1996, 118, 3869.
12. (a) Wasielewski, M. R.; Johnson, D. G.; Niemczyk, M. P.; Gaines, G. L., III; O'Neil, M. P.; Svec, W. A. J. Am. Chem. Soc. 1990, 112, 6482.
13. (b) Zheng, G.; Pandey, R. K.; Forsyth, T. P.; Kozyrev, A. N.; Dougherty, T. J.; Smith, K. M. Tetrahedron Lett. 1997, 38, 2409.
14. (a) Zheng, G.; Kozyrev, A. N.; Dougherty, T. J.; Smith, K. M.; Pandey, R. K. Chem. Lett. 1996, 1119.
15. (b) Zheng, G.; Dougherty, T. J.; Pandey, R. K. J. Org. Chem. 1999, 64, 3751.
16. 6, mesopurpurin-18, and mesopyropheophorbide a methyl esters.
17. Pandey, R. K.; Shiau, F.-Y.; Medforth, C. J.; Dougherty, T. J.; Smith, K. M. Tetrahedron Lett. 1990, 31, 789.
18. Purpurin-imides are a class of compounds derived from purpurin-18. In this series, the six-membered exocyclic anhydride ring fused at the meso position is replaced by an imide ring system.
19. (a) Sessler, J. L.; Johnson, M. R.; Creager, S. E.; Fettinger, J. C.; Ibers, J. A. J. Am. Chem. Soc. 1990, 112, 6482 and references therein.
20. (b) Harriman, A.; Sauvage, J. P. Chem. Soc. Rev. 1996, 41.
21. Gust, D.; Moore, T. A.; Bensasson, R. V.; Mathis, P.; Land, E. J.; Chachety, C.; Moore, A. L.; Liddell, P. A.; Nemeth, G. A. J. Am. Chem. Soc. 1985, 107, 3631.
22. 1Hs and the ring system were examined. The structure that provided the best agreement with the observed NOEs and the changes in the chemical shifts was selected as the possible 3D structure of dimer 4.
23. Yeates, T. O.; Komiy, H.; Chirino, A.; Rees, D. C.; Allen, J. P.; Feher, G. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 7993.
24. Ivashin, N.; Kallebring, B.; Larsson, S.; Hansson, O. J. Phys. Chem. B 1998, 102, 5017.
25. Kozyrev, A. N.; Pandey, R. K.; Medforth, C. J.; Zheng, G.; Dougheny, T. J.; Smith, K. M. Tetrahedron Lett. 1996, 37, 747.
26. 8 requires 1225.6364.