Illustrating atropisomerism in the porphyrin series using NMR spectroscopy

Analusis

Volumn 27, Issue 5, 1999, Pages 464-467

  Song, R ^a   Robert, A ^a   Bernadou, J ^a   Meunier, B ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

Analytical chemistry; Atropisomerism; NMR spectroscopy; Porphyrin

Indexed keywords

BIPHENYL DERIVATIVE; CARBON; ENZYME; HEME DERIVATIVE; METALLOPORPHYRIN; METHYL GROUP; PORPHYRIN DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 0032847353     PISSN: 03654877     EISSN: None     Source Type: Journal    
DOI: 10.1051/analusis:1999126     Document Type: Article

References (21)

1. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; chapter 14, pp 1119-1190.
2. Gottwald, L. K.; Ullman, E. F. Tetrahedron Lett. 1969, 36, 3071-3074.
3. Collman, J. P.; Gagne, R. R.; Reed, C. A.; Halbert, T. R.; Lang, G.; Robinson, W. T. J. Am. Chem. Soc. 1975, 97, 1427-1439.
4. Collman, J. P.; Brauman, J. I.; Collins, T. J.; Iverson, B. L.; Lang, G.; Pettman, R. B.; Sessler, J. L.; Walters, M. A. J. Am. Chem. Soc. 1983, 105, 3038-3052.
5. Maillard, P.; Guerquin-Kern, J. L.; Momenteau, M. J. Am. Chem. Soc. 1989, 111, 9125-9127.
6. Collman, J. P.; Halbert, T. R.; Suslick, K. S. In Metal Ion Activation of Oxygen; Spiro, T. G. Ed.; Wiley: New York, 1980; Vol. 1.
7. Momenteau, M.; Reed, C. A. Chem. Rev. 1994, 94, 659-698.
8. Fisher, H.; Orth, H. Akad. Verlagsgesellschaft, Leipzig, 1937, Vol II, Part 1.
9. When the tetrapyrrolic ligand is oriented with the numbering clockwise when seen from above, the groups below and above the plane are then designated by the use of α and β, respectively. See Moss, G. P. Nomenclature of tetrapyrroles Pure & Appl. Chem. 1987, 59, 779-832.
10. Drexler, C.; Hosseini, M. W.; Planeix, J. M.; Stupka, G.; De Cian, A.; Fisher, J. Chem. Commun. 1998, 689-690.
11. Walker, F. A. Tetrahedron Lett. 1971, 52, 4949-4952.
12. Eaton, S. S.; Eaton, G. R. J. Am. Chem. Soc. 1975, 97, 3660-3666.
13. Abraham, R. J.; Plant, J.; Bedford, G. R. Org. Magn. Reson. 1982, 19, 204-210.
14. Suslick, K. S.; Reinert, T. J. J. Chem. Educ. 1985, 62, 974.
15. Crossley, M. J.; Field, L. D.; Forster, A. J.; Hording, M. M.; Sternhell, S. J. Am. Chem. Soc. 1987, 109, 341-348.
16. Hoffmann, P.; Robert, A.; Meunier, B. Bull. Soc. Chim. Fr. 1992, 129, 85-97.
17. Hayashi, T; Asai, T.; Hokasono, H.; Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 12210-12211.
18. Rose, E.; Quelquejeu, M.; Pochet, C.; Julien, N.; Kossanyi, A.; Hamon, L. J. Org. Chem. 1993, 58, 5030-5031.
19. Beeston, R. F.; Stitzel, S. E.; Rhea, M. A. J. Chem. Educ. 1997, 74, 1468-1471.
20. Song, R.; Witvrouw, M.; Robert, A.; Balzarini, J.; De Clercq, E.; Bernadou, J.; Meunier, B. Antiviral Chem. Chemother. 1997, 8, 85-97.
21. Song, R.; Robert, A.; Bemadou, J.; Meunier, B. Inorg. Chim. Acta 1998, 272, 228-234.