The porphyrin twist: Hückel and Möbius aromaticity

Angewandte Chemie - International Edition

Volumn 47, Issue 14, 2008, Pages 2543-2546

  Jux, Norbert ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Aromaticity; Expanded porphyrins; M bius aromaticity; Porphyrinoids

Indexed keywords

CHEMICAL REACTIONS; PORPHYRINS; SOLID SOLUTIONS;

AROMATICITY; CHEMICAL EQUATIONS; CONFORMATIONAL FLEXIBILITY; EXPANDED PORPHYRINS; PORPHYRINOIDS; SOLID STATES;

MOLYBDENUM;

EID: 53549083545     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705568     Document Type: Review

References (43)

1. E. Heilbronner, Tetrahedron Lett. 1964, 5, 1923-1928.
2. M. Stȩpień, L. Latos-Grażyński, N. Sprutta, P. Chwalisz, L. Szterenberg, Angew. Chem. 2007, 119, 8015-8019;
3. Angew. Chem. Int. Ed. 2007, 46, 7869-7873.
4. See two excellent reviews on the topic of Möbius aromaticity: a) H. S. Rzepa, Chem. Rev. 2005, 105, 3697-3715;
5. b) R. Herges, Chem. Rev. 2006, 106, 4820-4842, and references therein.
6. D. Ajami, O. Oeckler, A. Simon, R. Herges, Nature 2003, 426, 819-821.
7. D. Ajami, K. Hess, F. Köhler, C. Näther, O. Oeckler, A. Simon, C. Yamamoto, Y. Okamoto, R. Herges, Chem. Eur. J. 2006, 12, 5434-5445.
8. C. Castro, Z. Chen, C. S. Wannere, H. Jiao, W. L. Karney, M. Mauksch, R. Puchta, N. J. R. van Eikema Hommes, P. von R. Schleyer, J. Am. Chem. Soc. 2005, 127, 2425-2432.
9. a) L. M. Jackman, F. Sondheimer, Y. Amiel, D. A. Ben-Efraim, Y. Gaoni, R. Wolovsky, A. A. Bothner-By, J. Am. Chem. Soc. 1962, 84, 4307-4312;
10. b) E. Vogel, W. Pretzer, W. A. Böll, Tetrahedron Lett. 1965, 6, 3613-3617;
11. c) E. Vogel, Pure Appl. Chem. 1993, 65 143-152.
12. a) H. König, C. Eickmeier, M. Möller, U. Rodewald, B. Franck, Angew. Chem. 1990, 102, 1437-1439;
13. Angew. Chem. Int. Ed. Engl. 1990, 29, 1393-1395;
14. b) S. Beckmann, T. Wessel, B. Franck, W. Hönle, H. Borrmann, H. G. von Schnering, Angew. Chem. 1990, 102, 1439-1441;
15. Angew. Chem. Int. Ed. Engl. 1990, 29, 1395-1397;
16. the nomenclature of expanded porphyrin was suggested by Franck and Nonn (B. Franck, A. Nonn, Angew. Chem. 1995, 107, 1941-1957;
17. Angew. Chem. Int. Ed. Engl. 1995, 34, 1795-1811)
18. and is given as: 1) a number in square brackets corresponding to the number of π electrons in the shortest main conjugation pathway, 2) a core name representing the number of pyrroles or other (hetero)cycles in the overall system, and 3) numbers in round brackets following the main name that specify the number of bridging carbon atoms between each pyrrole subunit, starting with the largest bridge.
19. a) M. Gosmann, B. Franck, Angew. Chem. 1986, 98, 1107-1108;
20. Angew. Chem. Int. Ed. Engl. 1986, 25, 1100-1101;
21. b) G. Knübel, B. Franck, Angew. Chem. 1988, 100, 1203-1211;
22. Angew. Chem. Int. Ed. Engl. 1988, 27, 1170-1172;
23. c) M. Bröring, H.-J. Dietrich, J. Dörr, G. Hohlneicher, J. Lex, N. Jux, C. Pütz, M. Roeb, H. Schmickler, E. Vogel, Angew. Chem. 2000, 112, 1147-1150;
24. Angew. Chem. Int. Ed. 2000, 39, 1105-1108.
25. a) C. J. Medforth in The Porphyrin Handbook, Vol. 5 (Eds: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 1-80;
26. b) F. A. Walker in The Porphyrin Handbook, Vol. 5 (Eds: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 81-174.
27. T. K. Chandrashekar, S. Venkatraman, Acc. Chem. Res. 2003, 36, 676-691.
28. J. L. Sessler, D. Seidel, Angew. Chem. 2003, 115, 5292-5333;
29. Angew. Chem. Int. Ed. 2003, 42, 5134-5175, and references therein.
30. a) R. Charriere, T. A. Jenny, H. Rexhausen, A. Gossauer, Heterocycles 1993, 36, 1561-1575;
31. b) M. Suzuki, A. Osuka, Org. Lett. 2003, 5, 3943-3946.
32. a) J.-Y. Shin, H. Furuta, K. Yoza, S. Igarashi, A. Osuka, J. Am. Chem. Soc. 2001, 123, 7190-7191;
33. b) S. Saito, A. Osuka, Chem. Eur. J. 2006, 12, 1923-1928.
34. A. Werner, M. Michels, L. Zander, J. Lex, E. Vogel, Angew. Chem. 1999, 111, 3866-3870;
35. Angew. Chem. Int. Ed. 1999, 38, 3650-3653.
36. R. Taniguchi, S. Shimizu, M. Suzuki, J.-Y. Shin, H. Furuta, A. Osuka, Tetrahedron Lett. 2003, 44, 2505-2507.
37. Y. Tanaka, S. Saito, S. Mori, N. Aratani, H. Shinokubo, N. Shibata, Y. Higuchi, Z. S. Yoon, K. S. Kim, S. B. Noh, J. K. Park, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 693-696;
38. Angew. Chem. Int. Ed. 2008, 47, 681-684.
39. a) J. D. Harvey, C. J. Ziegler, J. Inorg. Biochem. 2006, 100, 869-880;
40. b) P. J. Chmielewski, L. Latos-Grażyński, Coord. Chem. Rev. 2005, 249, 2510-2533.
41. S. Mori, S. Schimizu, R. Taniguchi, A. Osuka, Inorg. Chem. 2005, 44, 4127-4129.
42. C. Castro, C. M. Isborn, W. L. Karney, M. Mauksch, P. von R. Schleyer, Org. Lett. 2002, 4, 3431-3434.
43. And the story continues: In a recent publication Möbius-aromatic metal complexes of so-called N-confused porphyrins were reported; see J. K. Park, Z. S. Yoon, M.-C. Yoon, K. S. Kim, S. Mori, J.-Y. Shin, A. Osuka, D. Kim, J. Am. Chem. Soc. 2008, 130, 1824-1825.