Tautomerism in novel oxocorrologens

Chemistry - A European Journal

Volumn 13, Issue 35, 2007, Pages 9824-9833

  Xie, Yongshu ^a,d   Hill, Jonathan P ^a   Schumacher, Amy Lea ^b   Karr, Paul A ^b   D'Souza, Francis ^b   Anson, Christopher E ^c   Powell, Annie K ^c   Ariga, Katsuhiko ^a  

^a NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^b WICHITA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF KARLSRUHE   (Germany)

^d EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Corroles; N alkylation; Porphyrinoids; Quinones; Tautomerism

Indexed keywords

ALKYLATION; ELECTRONEGATIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; SOLVENTS; X RAY CRYSTALLOGRAPHY;

MACROCYCLIC NITROGEN; PORPHYRINOIDS; QUINONES; TAUTOMERISM;

KETONES;

EID: 37249088971     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701428     Document Type: Article

References (55)

1. a) M. B. Smith. J. March, in Advanced Organic Chemistry, 5th ed., Wiley Interscience, New York, 2001, pp. 1218-1223;
2. b) J. Elguero, C. Marzin, A. R. Katritzky, P. Linda, in The Tautomerism of Heterocycles. Adv. Heterocycl. Chem. Suppl. 1, Academic Press, New York, 1976.
3. a) H. Hart. Chem. Rev. 1979, 79, 515;
4. b) Z. Rappoport. in The Chemistry of Enols, Wiley, Chichester, UK, 1990.
5. For example, the case of histamine: F.J. Ramírez. I. Tuñón. A.J. Collado, E. Silla, J. Am. Chem. Soc. 2003. 125, 2328-2340, and references therein.
6. a) J. D. Watson. F. H. C. Crick, Nature 1953, 171. 737-738;
7. b) J. D. Watson. F. H. C. Crick, Nature 1953, 171, 964-967;
8. c) C. Colominas, F. J. Luque, M. Orozco. J. Am. Chem. Soc. 1996, 118, 6811 -6821.
9. a) P. Zuman, J. Michl, Nature 1961, 192. 655-657;
10. b) M. Boiani, H. Ccrecetto. M. González, O. E. Piro, E. E. Castellano, J. Phvs. Chem. A 2004, 108. 11241-11248;
11. c) P. Pérez, A. Toro-Labbé, J. Phys. Chem. A 2000. 104, 1557-1562.
12. V. Balzani, M. Venturi. A. Credi. in Molecular Devices and Machines, Wiley-VCH, Weinheim, 2003.
13. P. Liljeroth, J. Repp, G. Meyer, Science 2007, 317, 1203-1206.
14. a) P. Naumov. J. Mol. Struct. 2006, 783. 1-8;
15. b) P. Naumov, A. Sckine, H. Uekusa. Y. Ohashi, J. Am. Chem. Soc. 2002, 124, 8540-8541;
16. c) I. Renge, J. Lumin. 2000, 98, 213-220.
17. J. R. Reimers, L. E. Hall. N. S. Hush. K. Silverbrook. Ann. N. Y. Acad. Sci. 1998, 852, 38-53.
18. a) C. B. Storm. Y. Teklu, J. Am. Chem. Soc. 1972, 94, 1745-1747;
19. b) J. Braun. M. Koecher, M. Schlabach, B. Wehrle, H.-H. Limbach, E. Vogel, J. Am. Chem. Soc. 1994, 116, 6593-6604.
20. H. Furuta. T. Ishizuka. A. Osuka. H. Dejima, H. Nakagawa, Y. Ishikawa, J. Am. Chem. Soc. 2001, 123, 6207-6208.
21. a) R. Paolesse, in The Porphyrin Handbook, Vol.2 (Eds.: K.M. Kadish. K. M. Smith, R. Guilard). Academic Press, San Diego, 2003, pp. 201-232;
22. b) R. Guilard, J.-M. Barbe, C. Stern. K. M. Kadish. in The Porphyrin Handbook, Vol. 18 (Eds.: K. M. Kadish. K. M. Smith. R. Guilard), Academic Press. San Diego. 2003, pp. 303.
23. For example: a) G. Golubkov, Z. Gross, J. Am. Chem. Soc. 2005, 127. 3258-3259;
24. b) J. P. Coliman, M. Kaplun, R. A. Decreau, Dalton Trans. 2006. 554-559;
25. c) J.-M. Barbe, G. Canard, S. Brandes, F. Jérôme. G. Dubois, R. Guilard, Dalton Trans. 2004, 1208-1214.
26. I. Aviv. Z. Gross. Chem. Commun. 2007, 1987-1999.
27. a) Z. Gross. N. Galili. I. Saltsman. Angew. Chem. 1999, 111, 1530- 1533;
28. Angew. Chem. Int. Ed. 1999, 38, 1427-1429;
29. b) R. Paolesse, L. Jaquinod. D. J. Nurco, S. Mini, F. Sagone, T. Boschi, K. M. Smith, Chem. Commun. 1999. 1307-1308;
30. c) D. T. Gryko, Eur. J. Org. Chem. 2002, 1735-1743.
31. Some rare examples of multiple protropic tautomerism: a) L. Szterenberg, L. Latos-Grażyñski. J. Phys. Chem. A 1999, 103, 3302-3309;
32. b) K. Rachlewicz, N. Sprutta, P. J. Chmielewski. L. Latos- Grażyñski, J. Chem. Soc. Perkin Trans. 2 1998, 969-975;
33. c) H. Komber. H.-H. Limbach. E. Böhme. C. Kunert, J. Am. Chem. Soc. 2002, 124, 11955-11963.
34. Corroie itself displays some propensity for tautomerism depending on its substituents: T. Ding, J. D. Harvey, C. J. Ziegler, J. Porphyrins Phthalocyanines 2004, 9, 22-27.
35. a) L. R. Milgrom, Tetrahedron 1983, 39, 3895-3898;
36. b) A. J. Golder. L. R. Milgrom, K. B. Nolan. D. C. Povey, J. Chem. Soc. Chem. Commun. 1989, 1751-1753.
37. a) L. R. Milgrom, J. P. Hill, W. D. Flitter, J. Chem. Soc. Perkin Trans. 2 1994, 521-524;
38. b) L. R. Milgrom, J. P. Hill, J. Heterocycl. Chem. 1993, 30, 1629-1633;
39. c) L. R. Milgrom. XP. Hill. W.D. Flitter. J. Chem. Soc. Chem. Commun. 1992, 773.
40. J. P. Hill, A. L. Schumacher, F. D'Souza, J. Labuta, C. Redshaw, M. J. R. Elsegood, M. Aoyagi, T. Nakanishi, K. Ariga, Inorg. Chem. 2006, 45, 8288-8296.
41. M. S. Somma, C. J. Medforth, N. Y. Nelson, M. M. Olmstead. R. G. Khoury, K. M. Smith, Chem. Commun. 1999, 1221-1222.
42. Tautomeric switching between aromatic and anti-aromatic states of a 22-hydroxybenziporphyrin has recently been reported: M. Stepieñ, L. Latos-Grażyñski, L. Szterenberg J. Org. Chem. 2007, 72. 2259-2270.
43. S. Shimokawa, H. Fukui, J. Sohma, Mol. Phys. 1970, 19, 695-702.
44. a) L. R. Milgrom, J. P. Hill, P. Dempsey, Tetrahedron 1994, 50, 13477-13484;
45. b) L. R. Milgrom, J. P. Hill, G. Yahioglu, J. Heterocycl. Chem. 1995, 32, 97-101;
46. c) J. P. Hill, I. J. Hewitt, C. E. Anson, A. K. Powell, A. L. McCarthy, P. Karr, M. Zandler, F. D'Souza. J. Org. Chem. 2004, 69, 5861-5869;
47. d) J. P. Hill, W. Schmitt, A. L. McCarty, K. Ariga. F. D'Souza, Eur. J. Org. Chem. 2005, 2893-2902;
48. e) J. P. Hill, A. S. D. Sandanayaka. A. L. McCarty, P. A. Karr, M. E. Zandler, R. Charvet, K. Ariga, Y. Araki, O. Ito, F. D'Souza, Eur. J. Org. Chem. 2006, 595-603.
49. The related N-alkyl corroles are also known: Z. Gross, N. Galili, Angew. Chem. 1999, 111, 2536-2540;
50. Angew. Chem. Int. Ed. 1999, 38, 2366-2369, and references therein.
51. a) J. S. Connolly, J. R. Bolton, in Photoinduced Electron Transfer, Part D (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, pp. 303-393;
52. b) M. E. El-Khouly, O. Ito, P. M. Smith, F. D'Souza. J. Photochem. Photobiol. C 2004, 5, 79-104.
53. G. M. Sheldrick, SHELXTL 6.14, Bruker AXS Inc., 6300 Enterprise Lane, Madison, WI 53719-1173, USA (2003).
54. A. L. Spek, PLATON - A Multipurpose Crystallographic Tool, Utrecht University, Utrecht (The Netherlands), 2002;
55. P. van der Sluis, A. L. Spek, Acta Crystallogr. 1990, A46. 194.