Highly selective chlorosulfonation of tris(pentafluorophenyl)corrole as a synthetic tool for the preparation of amphiphilic corroles and metal complexes of planar chirality

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3443-3446

  Mahammed, Atif ^a   Goldberg, Israel ^b   Gross, Zeev ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; CORROLE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; METALLOPORPHYRIN; PORPHYRIN; TRIS(PENTAFLUOROPHENYL)CORROLE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

COBALT; CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; METALLOPORPHYRINS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PORPHYRINS; STEREOISOMERISM;

EID: 0035515328     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0163878     Document Type: Article

References (38)

1. (a) Sternberg, E. D.; Dolphin, D.; Bruckner, C. Tetrahedron 1998, 54, 4151.
2. (b) Sessler, J. L.; Weghorn, S. J. Expanded, Contracted, & Isomeric Porphyrins; Pergamon: Oxford, 1997.
3. (c) Metalloporphyrins Catalyzed Oxidations; Montanari, F., Casella, L., Eds.; Kluwer Academic Publishers: Dordrecht, 1994.
4. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19.
5. Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E.; Brauman, J. I. Science 1993, 261, 1404.
6. Lindsey, J. S. In The Porphyrin Handbook, Vol. I; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000; Chapter 2, pp 45-118.
7. Paolesse, R. In The Porphyrin Handbook, Vol. II; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000; Chapter 11, pp 201-232.
8. (a) Gross, Z.; Galili, N.; Saltsman, I. Angew. Chem., Int. Ed. 1999, 38, 1427.
9. (b) Paolesse, R.; Jaquinod, L.; Nurco, D. J.; Mini, S.; Sagone, F.; Boschi, T.; Smith, K. M. Chem. Commun. 1999, 1307.
10. (c) Cho, W.-S.; Lee, C.-H. Tetrahedron Lett. 2000, 41, 697.
11. (d) Gryko, D. T. Chem. Commun. 2000, 2243.
12. (e) Briñas, R. P.; Brückner, C. Synlett 2001, 442.
13. (a) Gross, Z.; Simkhovich, L.; Galili, N. Chem. Commun. 1999, 599.
14. (b) Gross, Z.; Golubkov, G.; Simkhovich, L. Angew. Chem., Int. Ed. 2000, 39, 4045.
15. (c) Simkhovich, L.; Mahammed, A.; Goldberg, I.; Gross, Z. Chem. Eur. J. 2001, 7, 1041.
16. Aviezer, D.; Cotton, S.; David, M.; Segev, A.; Khaselev, N.; Galili, N.; Gross, Z.; Yayon, A. Cancer Res. 2000, 60, 2973.
17. Gross, Z.; Galili, N. Angew. Chem., Int. Ed. 1999, 38, 2366.
18. (a) Gross, Z.; Galili, N.; Simkhovich, L.; Saltsman, I.; Botoshansky, M.; Blaser, D.; Boese, R.; Goldberg, I. Org. Lett. 1999, 1, 599.
19. (b) Bendix, J.; Gray, H. B.; Golubkov, G.; Gross, Z. Chem. Commun. 2000, 1957.
20. (c) Simkhovich, L.; Galili, N.; Saltsman, I.; Goldberg, I.; Gross, Z. Inorg. Chem. 2000, 39, 2704.
21. (d) Meier-Callahan, A. E.; Gray, H. B.; Gross, Z. Inorg. Chem. 2000, 39, 3605.
22. (e) Mahammed, A.; Goldberg, I.; Gross, Z. Chem. Eur. J. 2001, 7, 4259.
23. (a) Mansuy, D. Coord. Chem. Rev. 1993, 125, 129.
24. (b) Gross, Z.; Simkhovich, L. Tetrahedron Lett. 1998, 39, 8171.
25. (a) Erben, C.; Will, S.; Kadish, K. M. In The Porphyrin Handbook, Vol. II; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000; Chapter 12, pp 233-300.
26. (b) Bendix, J.; Dmochowski, I. J.; Gray, H. B.; Mahammed, A.; Simkhovich, L.; Gross, Z. Angew. Chem., Int. Ed. 2000, 39, 4048.
27. Paolesse, R.; Nardis, S.; Sagone, F.; Khoury, R. G. J. Org. Chem. 2001, 66, 550.
28. Golubkov, G.; Bendix, J.; Gray, H. B.; Mahammed, A.; Goldberg, I.; DiBilio, A. J.; Gross, Z. Angew. Chem., Int. Ed. 2001, 34, 2132.
29. Palacio, M.; Mansuy-Mouries, V.; Loire, G.; Barch-Ozett, K.; Leduce, P.; Barkigia, K. M.; Fajer, J.; Battion, P.; Mansuy, D. Chem. Commun. 2000, 1907.
30. Rocha Gonsalves, A. M. A.; Johnson, R. A. W.; Pereira, M. M.; SantAna, A. M. P.; Serra, A. C.; Sobral, A. J. F. N. Heterocycles 1996, 43, 829.
31. Gregory, P. J. Porphyrins Phthalocyanines 2000, 4, 432.
32. -.
33. 6) δ = -136.7 (d, J = 24.7 Hz, 2F), -137.2 (d, J = 25.0 Hz, 2F), -137.7 (d, J = 21.8 Hz, 1F), -139.7 (d, J = 23.4 Hz, 1F), -152.2 (t, J = 21.7, 1F), -154.3 (t, J = 21.3, 2F), -161.3 (m, 4F), -164.2 (m, 2F).
34. Farnier, M.; Soth, S.; Fournari, P. Can. J. Chem. 1976, 54, 1083.
35. Blackburg, B. K.; Davies, S. G.; Whittacker, M. In Stereochemistry of Organometallic and Inorganic Compounds, Vol. 3; Bernal, I., Ed.; Elsevier: Amsterdam, 1989; p 141.
36. w = 0.160) for all the unique data.
37. -1)) = 414 (71 000), 430 (62 000), 588 (15 000), 620 (27 000).
38. Bishop, S. M.; Khoo, B. J.; MacRobert, A. J.; Simpson, M. S. C.; Philips, D.; Beeby, A. J. Chromatogr. 1993, 646, 345.