First synthesis of tetrapyrrolylporphyrin

Organic Letters

Volumn 2, Issue 2, 2000, Pages 187-189

  Furuta, Hiroyuki ^a,b   Maeda, Hiromitsu ^a   Furuta, Takahiro ^b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b OITA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042911904     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9912783     Document Type: Article

References (21)

1. (a) Lindsey, J. S. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds; Academic Press: San Diego, 1999; Vol. 1, Chapter 2.
2. (b) Jaquinod, L., ref 1a, Chapter 5.
3. (a) Stibrany, R. T.; Vasudevan, J.; Knapp, S.; Potenza, J. A.; Emge, T.; Schugar, H. J. J. Am. Chem. Soc. 1996, 118, 3980-3981.
4. (b) Schenning, A. P. H. J.; Benneker, F. B. G.; Geurts, H. P. M.; Liu, X. Y.; Nolte, J. M. J. Am. Chem. Soc. 1996, 118, 8549-8552.
5. (c) Kobuke, Y.; Miyaji, H. Bull. Chem. Soc. Jpn. 1996, 69, 3563-3569.
6. Mono- and dipyrrolylporphyrins and their derivatives were reported. (a) Clezy, P. S.; Liepa, A. J.; Webb, N. W. Aust. J. Chem. 1972, 25, 1991-2001.
7. (b) Aota, H.; Itai, Y.; Matsumoto, A.; Kamachi, M. Chem. Lett. 1994, 2043-2046.
8. (c) Aota, H.; Reikan, T.; Matsumoto, A.; Kamachi, M. Chem. Lett. 1998, 335-336.
9. Furuta, H.; Maeda, H.; Osuka, A. J. Am. Chem. Soc. In press.
10. Differentiations between αβββ (2) and αααβ (5) are based on the chemical shifts (ppm) of meso pyrroles: α-linked (7.52, 8.40); β-linked (8.20, 8.35). We think the ring current effect differs greatly for α- and β-H of an α-linked pyrrole but are similar for a β-linked pyrrole.
11. 1H NMR spectra of selected TPyrP derivative are shown in the Supporting Information.
12. 2O: C, 71.87; H, 6.03; N, 12.89. Found: C, 72.26; H, 6.00; N. 12.50. The synthetic details and the spectral data of TPyrPs are shown in the Supporting Information.
13. Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell, T. T.; Artis, D. R.; Muchowski, J. M. J. Org. Chem. 1990, 55, 6317-6328.
14. w = 0.063, GOF = 2.03. We would like to thank Dr. Takuji Ogawa at Ehime University for initial help with the X-ray structural work.
15. Silvers, S. J.; Tulinsky, A. J. Am. Chem. Soc. 1967, 89, 3331-3337.
16. max[nm] 454.5, 767.5.
17. 3 was too broad to get the details about the conformational change upon protonation.
18. (a) Franck, B.; Nonn, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1795-1811.
19. (b) Bonnett, R. Chem. Rev. 1995, 95, 19-33.
20. (c) Sternberg, E. D.; Dolphin, D.; Bruckner, C. Tetrahedron 1998, 54, 4151-4202.
21. (d) Pandy, R.; Gang, G. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds; Academic Press: San Diego, 1999; Vol. 6, Chapter 43.