Phosphorus complexes of the first expanded isophlorins

Chemistry - A European Journal

Volumn 16, Issue 1, 2010, Pages 55-59

  Miura, Takahiro ^a   Higashino, Tomohiro ^a   Saito, Shohei ^a   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aromaticity; Expanded porphyrins; Isophlorin; Phosphorus

Indexed keywords

AROMATICITIES; CHEMICAL EQUATIONS; EXPANDED PORPHYRINS; INTERCONVERSIONS; OCTAPHYRINS;

CHEMICAL REACTIONS; PORPHYRINS;

PHOSPHORUS;

EID: 73949096721     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902708     Document Type: Article

References (35)

1. R. B. Woodward, Angew. Chem. 1960, 72, 651-662.
2. a) M. Pohl, H. Schmickler, J. Lex, E. Vogel, Angew. Chem. 1991 103, 1737-1741
3. Angew. Chem. Int. Ed. Engl. 1991, 30, 1693-1697
4. b) J. Setsune, K. Kashihara, K. Wada, H. Shiozaki, Chem. Lett. 1999, 847-848.
5. a) J. A. Cissell, T. P. Vaid, A. L. Rheingold, J. Am. Chem. Soc. 2005, 127, 12212-12213
6. b) C. Liu, D.-M. Shen, Q.-Y. Chen, J. Am. Chem. Soc. 2007, 129, 5814-5815
7. c) J. A. Cissell, T. P. Vaid, G. P. A. Yap, J. Am. Chem. Soc. 2007, 129, 7841-7847
8. d) A. Weiss, M. C. Hodgson, P. D.W. Boyd, W. Siebert, P. J. Brothers, Chem. Eur. J. 2007, 13, 5982-5993
9. e) Y. Matano, M. Nakashima, T. Nakabuchi, H. Imahori, S. Fujishige, H. Nakano, Org. Lett. 2008, 10, 553-556.
10. Y. Yamamoto, A. Yamamoto, S. Furuta, M. Horie, M. Kodama, W., Sato, K. Akiba, S. Tsuzuki, T. Uchimaru, D. Hashizume, F. Iwasakai, J. Am. Chem. Soc. 2005, 127, 14540-14541.
11. a) A. Jasat, D. Dolphin, Chem. Rev. 1997, 97, 2267-2340
12. b) T. D., Lash, Angew. Chem. 2000, 112, 1833-1837
13. Angew. Chem. Int. Ed. 2000, 39, 1763-1767
14. c) H. Furuta, H. Maeda, A. Osuka, Chem. Commun. 2002, 1795-1804
15. d) J. L. Sessler, D. Seidel, Angew. Chem. 2003, 115, 5292-5333
16. Angew. Chem. Int. Ed. 2003, 42, 5134-5175
17. e)T. K. Chandrashekar, S. Venkatraman, Acc. Chem. Res. 2003, 36, 676-691
18. f) A. Ghosh, Angew. Chem. 2004, 116, 1952-1965
19. Angew. Chem. Int. Ed. 2004, 43, 1918-1931
20. g) S. Shimizu, A. Osuka, Eur. J. Inorg. Chem. 2006, 1319-1335
21. h) J. M. Lim, Z. S. Yoon, J.-Y. Shin, K. S. Kim, M.-C. Yoon, D. Kim, Chem. Commun. 2009, 261-273.
22. J. S. Reddy, S. Mandai, V. G. Anand, Org. Lett. 2006, 8, 5541-5543
23. a) J.-Y. Shin, H. Furuta, K. Yoza, S. Igarashi, A. Osuka, J. Am. Chem. Soc. 2001, 123, 7190-7191
24. b) R. Taniguchi, S. Shimizu, M. Suzuki, J.-Y. Shin, H. Furuta, A. Osuka, Tetrahedron Lett. 2003, 44, 2505-2507
25. c) For tetrathia[36]- and [38]octaphyrins(1.1.1.1.1.1.1.1), see: N. Sprutta, L. Latos-Grazyński, Chem. Eur. J. 2001, 7, 5099-5112.
26. a) H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 1999, 121, 2945-2946
27. b) H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 2000, 122, 5748-5757.
28. a) A. Młodzianowska, L. Latos-Grazyński, L. Szterenberg, Inorg. Chem. 2008, 47, 6364-6374
29. b) E. Pacholska-Dudziak, F. Ulatowski, Z. Ciunik, L. Latos- Grazyński, Chem. Eur. J. 2009, 15, 10924-10929.
30. w = 0.2554 (all data); GOF = 0.969
31. w = 0.2658 (all data); GOF = 0.949
32. [13] CCDC-747644 (2), 747646 (3) and 747645 (5) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif http://www.ccdc.cam.ac.uk/ data-request/cif.
33. D. B. Chesnut, L. D. Quin, Tetrahedron 2005, 61, 12343-12349.
34. The signal due to the ß proton of pyrrole C was observed at δ = 7.43 ppm despite its location at the inner side of the macrocycle. This can be explained by the downfield shift derived from inductive electron-withdrawing effect of phosphoramide group.
35. PLATON, a multipurpose crystallographic tool, Utrecht University, Utrecht; A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.