Formation and properties of cyclo[6]pyrrole and cyclo[7]pyrrole

Journal of the American Chemical Society

Volumn 125, Issue 23, 2003, Pages 6872-6873

  Köhler, Thomas ^a   Seidel, Daniel ^a   Lynch, Vincent ^a   Arp, Forrest O ^a   Ou, Zhongping ^b   Kadish, Karl M ^b   Sessler, Jonathan L ^a  

^a The University of Texas at Austin   (United States)

^b University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; CONJUGATION; ENERGY; HYDROGEN BOND; MOLECULAR INTERACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0038277031     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035089y     Document Type: Article

References (24)

1. Jasat, A.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
2. (a) Sessler, J. L.; Weghorn, S. J. Expanded, Contracted & Isomeric Porphyrins; Pergamon: New York, 1997; Vol 15.
3. (b) Sessler, J. L.; Gebauer, A.; Weghorn, S. J. In The Porphyrin Handbook; Kadish, K., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; Chapter 9.
4. Sessler, J. L.; Seidel, D. Angew. Chem., Int. Ed. 2003, in press.
5. (a) Sessler, J. L.; Davis, J. M.; Acc. Chem. Res. 2001, 34, 989.
6. (b) Nishimoto, J.; Yamada, T.; Tabata, M., Anal. Chim. Acta 2001, 428, 201.
7. (c) Sessler, J. L., Sansom, P. I.; Andrievsky, A.; Kral, V. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., Garcia-Espana, E., Eds; VCH Verlag: Weinheim, 1997; pp 355-419.
8. (a) Sessler, J. L.; Seidel, D.; Vivian A. E.; Lynch, V.; Scott B. L., Keogh D. W.; Angew. Chem., Int. Ed. 2001, 40, 591.
9. (b) Sessler, J. L., Vivian, A. E.; Seidel, D.; Burrell, A. K.; Hoehner, M.; Mody, T. D.; Gebauer, A.; Weghorn S. J.; Lynch, V. Coord. Chem. Rev. 2001, 216, 411-434.
10. Pushpan, S. K.; Anand, V. R. G.; Venkatraman, S.; Srinivasan, A.; Gupta, A. K.; Chandrashekar, T. K. Tetraheron Lett. 2001, 42, 3391.
11. (a) Sessler, J. L.; Seidel, D.; Lynch, V. J. Am. Chem. Soc. 1999, 121, 11257-11258.
12. (b) Falk H.; Flödl H. Monatsh. Chem. 1988, 119, 247.
13. Recent publications concerning Rothemund condensations: (a) Shimizu, S.; Shin, J.-Y.; Furuta, H.; Ismael, R.; Osuka, A. Angew. Chem., Int. Ed. 2003, 42, 78-82. (b) Shin, J.-Y., Furuta, H.; Osuka, A. Angew. Chem., Int. Ed. 2001, 40, 619.
14. Recent publications concerning Rothemund condensations: (a) Shimizu, S.; Shin, J.-Y.; Furuta, H.; Ismael, R.; Osuka, A. Angew. Chem., Int. Ed. 2003, 42, 78-82. (b) Shin, J.-Y., Furuta, H.; Osuka, A. Angew. Chem., Int. Ed. 2001, 40, 619.
15. Examples of expanded porphyrins prepared using MacDonald condensations: (a) Srinivasan, A.; Mahajan, S.; Pushpan, S. K.; Ravikumar, M.; Chandrashekar, T. K. Tetrahedron Lett. 1998, 39, 1961. (b) Srinivasan, A.; Pushpan, S. K.; Ravikumar, M.; Chandrashekar, T. K.; Roy, R. Tetrahedron 1999, 55, 6671-6680.
16. Examples of expanded porphyrins prepared using MacDonald condensations: (a) Srinivasan, A.; Mahajan, S.; Pushpan, S. K.; Ravikumar, M.; Chandrashekar, T. K. Tetrahedron Lett. 1998, 39, 1961. (b) Srinivasan, A.; Pushpan, S. K.; Ravikumar, M.; Chandrashekar, T. K.; Roy, R. Tetrahedron 1999, 55, 6671-6680.
17. Seidel, D.; Lynch, V. M.; Sessler J. L. Angew. Chem., Int. Ed. 2002, 41, 1422-1425.
18. While the formation of the cyclo[6]pyrrole species 3 is easy to understand, the formation of the cyclo[7]pyrrole 4 is more difficult to rationalize. It could be the result of an attack by a bipyrrole radical, generated in situ, on a 2,2′-bond of a bipyrrole. Such a process would lead to the loss of one pyrrole unit and permit formation of 4.
19. w = 0.121. with a conventional R = 0.051. For details, see Supporting Information.
20. w = 0.198, with a conventional R = 0.078. For details, see Supporting Information.
21. -1 for the bis-HCl salts of 3, 4, and 1, respectively); we rationalize this in terms of the varying, albeit small, deviations from planarity seen for these systems.
22. Kadish, K. M.; Royal, G.; v. Caemelbaecke, E.; Gueletti, L. In The Porphyrin Handbook; Kadish, K., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; pp 1-219.
23. Fuhrhop, J. H.; Kadish, K. M.; Davis, D. G. J. Am. Chem. Soc. 1973, 95, 5140.
24. See footnote 37 in ref 10.