Two-step synthesis of stable dioxadicarbaporphyrins from bis(3-indenyl)METHANE

Angewandte Chemie - International Edition

Volumn 51, Issue 43, 2012, Pages 10871-10875

  Lash, Timothy D ^a   Lammer, Aaron D ^a   Ferrence, Gregory M ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

aromaticity; bridged annulenes; carbaporphyrins; fulvenes; indenes

Indexed keywords

ANNULENES; AROMATICITIES; CARBAPORPHYRINS; FULVENES; INDENES;

METHANE; POLYCYCLIC AROMATIC HYDROCARBONS; PORPHYRINS;

AROMATIC COMPOUNDS;

CYCLOPENTANE DERIVATIVE; FULVENE; INDENE; INDENE DERIVATIVE; METHANE; PORPHYRIN; PYRROLE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLOPENTANES; INDENES; METHANE; MOLECULAR CONFORMATION; PORPHYRINS; PYRROLES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84867522653     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201206385     Document Type: Article

References (28)

1. T. D. Lash, S. A. Jones, G. M. Ferrence, J. Am. Chem. Soc. 2010, 132, 12786-12787.
2. T. D. Lash, J. Porphyrins Phthalocyanines 2011, 15, 1093-1115.
3. Y. Nakagami, R. Sekine, J.-i. Aihara, Org. Biomol. Chem. 2012, 10, 5219-5229.
4. E. Vogel, J. Heterocycl. Chem. 1996, 33, 1461-1487.
5. T. D. Lash, Synlett 2000, 279-295.
6. T. D. Lash, Eur. J. Org. Chem. 2007, 5461-5481.
7. J.-i. Aihara, M. Makino, Org. Biomol. Chem. 2010, 8, 261-266.
8. See also:, E. Pacholska-Dudziak, L. Szterenberg, L. Latos-Grazynski, Chem. Eur. J. 2011, 17, 3500-3511.
9. T. D. Lash, M. J. Hayes, Angew. Chem. 1997, 109, 868-870
10. Angew. Chem. Int. Ed. Engl. 1997, 36, 840-842
11. T. D. Lash, M. J. Hayes, J. D. Spence, M. A. Muckey, G. M. Ferrence, L. F. Szczepura, J. Org. Chem. 2002, 67, 4860-4874
12. D. Liu, T. D. Lash, J. Org. Chem. 2003, 68, 1755-1761.
13. T. D. Lash, J. L. Romanic, M. J. Hayes, J. D. Spence, Chem. Commun. 1999, 819-820.
14. S. R. Graham, D. A. Colby, T. D. Lash, Angew. Chem. 2002, 114, 1429-1432
15. Angew. Chem. Int. Ed. 2002, 41, 1371-1374.
16. For examples of resorcinol-derived dicarbaporphyrinoids, see:, L. Xu, T. D. Lash, Tetrahedron Lett. 2006, 47, 8863-8866.
17. H. Furuta, H. Maeda, A. Osuka, J. Am. Chem. Soc. 2000, 122, 803-807
18. H. Maeda, A. Osuka, H. Furuta, J. Am. Chem. Soc. 2003, 125, 15690-15691.
19. Heterodicarbaporphyrinoids with alternating azulene and furan or thiophene rings have also been reported
20. N. Sprutta, M. Swiderska, L. Latos-Grazynski, J. Am. Chem. Soc. 2005, 127, 13108-13109
21. N. Sprutta, M. Siczek, L. Latos-Grazynski, M. Pawlicki, L. Szterenberg, T. Lis, J. Org. Chem. 2007, 72, 9501-9509.
22. T. D. Lash, D. A. Colby, A. S. Idate, R. N. Davis, J. Am. Chem. Soc. 2007, 129, 13800-13801
23. T. D. Lash, A. D. Lammer, A. S. Idate, D. A. Colby, K. White, J. Org. Chem. 2012, 77, 2368-2381.
24. Z. Zhang, G. M. Ferrence, T. D. Lash, Org. Lett. 2009, 11, 101-104.
25. T. D. Lash, J. A. El-Beck, D. A. Colby, J. Org. Chem. 2009, 74, 8830-8833
26. N. Sprutta, S. Mackowiak, M. Kocik, L. Szterenberg, T. Lis, L. Latos-Grazynski, Angew. Chem. 2009, 121, 3387-3391
27. Angew. Chem. Int. Ed. 2009, 48, 3337-3341.
28. H. Li, C. L. Stern, T. J. Marks, Macromolecules 2005, 38, 9015-9027.