Synthesis and characterization of a stable smaragdyrin isomer

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 7062-7065

  Sessler, Jonathan L ^a   Davis, Julian M ^a   Lynch, Vincent ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000106715     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981019b     Document Type: Article

References (21)

1. Woodward, R. B. Aromaticity: An International Symposium Sheffield, 1966, Special Publication no. 21; The Chemical Society: London, 1966.
2. Broadhurst, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc., Perkin Trans, 1 1972, 2111-2116.
3. Sessler, J. L.; Lisowski, J.; Boudreaux, K. A.; Lynch, V.; Barry, J.; Kodadek, T. A. J. Org. Chem. 1995, 60, 5975-5978.
4. Jasat, A.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
5. Brükner, C.; Sternberg, E. D.; Boyle, R. W.; Dolphin, D. Chem. Commun. 1997, 1689-1690.
6. Sessler, J. L.; Cyr, M. J.; Burrell, A. K. Synlett 1991, 127-134.
7. Sessler, J. L.; Weghorn, S. J. Expanded, Contracted, and Isomeric Porphyrins; Eisevier: Oxford, 1997.
8. Chmielewski, P. J.; Latos-Grazynski, L.; Rachlewicz, K. Chem. Eur. J. 1995, 1, 68-73.
9. Sessler, J. L.; Cyr, M. J.; Lynch, V.; McGee, E.; Ibers, J. A. J. Am. Chem. Soc. 1990, 112, 2813-2814.
10. Iverson, B. L.; Shreder, K.; Kral, V.; Sansom, P.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1608-1616.
11. Sessler, J. L.; Cyr, M. J.; Lynch, V. J. Am. Chem. Soc. 1990, 112, 2810-2813.
12. Shionoya, M.; Furuta, H.; Lynch, V.; Harriman, A.; Sessler, J. L. J. Am. Chem. Soc. 1992, 114, 5714-5722.
13. Davis, J. M. A. Ph. D. Thesis, University of Texas at Austin, 1998. Briefly, the condensation of appropriate precursors led to the formation of a dark green species, presumed to be smaragdyrin, that displayed a UV-vis absorption maximum at ca. 453 nm. This finding, in conjunction with 'H NMR data for the partially purified species, is consistent with the proposed pentapyrrolic, 22 .-r-electron system. However, no further characterization in our hands proved possible due to the rapid decomposition of the product when exposed to air.
14. Sessler, J. L.; Hugdahl, J.; Johnson, M. R. J. Org. Chem. 1986, 57, 2838-2840 and references cited therein.
15. Sessler, J. L.; Weghorn, S. J.; Lynch, V.; Hisaeda, Y. Chem. Eur. J. 1995, 1, 56.
16. Miller, D. C.; Johnson, M. R.; Becker, J. J.; Ibers, J. A. J. Heterocyd. Chem. 1993, 30, 1485.
17. Danso-Danquah, R. E.; Xie, L. Y.; Dolphin, D. Heteroc)-cles 1995, 41, 2553-2562.
18. Bauer, V. J.; Clive, D. L.; Dolphin, D.; Paine, J. B.; Harris, F. L.; King, M. M.; Loder, J.; Wang, S.-W. C.; Woodward, R. B. J. Am. Chem. Soc. 1983, 705, 6429-6436.
19. Interestingly, in the case of the sapphyrins, the pentaaza macrocycle has a more intense Soret-like band than the monoxa analogue. See: Sessler, J. L.; Hoehner, M. C.; Gebauer, A.; Andrievsky, A.; Lynch, V. J. Org. Chem. 1997, 62, 9251-9260.
20. Sessler, J. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 1348-1350.
21. Weghorn, S. J.; Lynch, V.; Sessler, J. L. Tetrahedron Lett. 1995, 36, 4713-4716.