H. Sharghi, A. Hassani Nejad / Tetrahedron 60 (2004) 1863–1868
1867
3.1.7. 5,10,15,20-Tetrakis(p-nitrophenyl)porphyrin (7).
Purple crystal; mp .300 8C; yield¼34%; spectroscopic
References and notes
data identical to that reported in the literature.23
1. For a remarkable book on porphrin history, chemistry and
applications, see. In The chemical and physical behavior of
porphyrin compounds and related structures. Annales New
York academy science; Adler, A. D., Ed.;, 1973; Vol. 206.
2. For a review, (a) Mlodnicka, T. J. Mol. Catal. 1986, 36, 205.
(b) Haslam, E. Shikimic acid metabolism and metabolites;
Wiley: New York, 1993. (c) Wijesekera, T. P.; Dolphin, D. In
Metalloporphyrins in catalytic oxidations; Sheldon, R. A.,
Ed.; Marcel Dekker: New York, 1994; pp 193–231.
3. Mansuy, D. Coord. Chem. Rev. 1993, 129.
3.1.8. 5,10,15,20-Tetrakis(p-isopropylphenyl)porphyrin
(8). Purple crystal; mp .300 8C; yield¼60%; [Found: C,
85.78; H, 6.61; N, 7.43. C56H54N4 requires C, 85.93; H,
6.90; N, 7.16%]; lmax (benzene; log 1): 420 nm (5.72), 489
(3.32), 518 (4.23), 520 (4.04), 599 (3.95), 652 (4.32). dH
(250 MHz, CDCl3): 22.74 (br. s 2NH); 1.40 (d, 24H,
J¼4.4 Hz, 8Me); 3.2 (m, 4CH); 7.55 (d, 8Hm); 8.02 (d, 8Ho);
8.83 (s, 8H (pyrrole)).
4. Metalloporphyrin catalyzed oxidation; Montanari, F., Cassela,
L., Eds.; Kluwer: Dordrecht, 1994.
3.1.9. 5,10,15,20-Tetrakis(m-methylphenyl)porphyrin
(9). Purple crystal; mp .300 8C; yield¼57%; spectroscopic
data identical to that reported in the literature.23
5. (a) Sharghi, H.; Naeimi, H. J. Chem. Res. (S) 1999, 310.
(b) Shamsipur, M.; Soleymanpour, A.; Akhond, M.; Sharghi,
H.; Hasaninejad, A. R. Sens. Actuators, B 2003, 89, 9.
6. (a) Drain, C. M.; Lehn, J. M. J. Chem. Soc. Chem. Commun.
1994, 2313. (b) Drain, C. M.; Russell, K. C.; Lehn, J. M.
J. Chem. Soc. Chem. Commun. 1996, 2337.
3.1.10. 5,10,15,20-Tetrakis(m-methoxyphenyl)porphyrin
(10). Purple crystal; mp .300 8C; yield¼40%; [Found: C,
78.37; H, 5.24; N, 7.65. C48H38N4O4 requires C, 78.45; H,
5.21; N, 7.62%]; lmax (benzene; log 1): 418 (5.73), 518
(4.09), 550 (3.95), 589 (3.91), 650 (3.90). dH (250 MHz,
CDCl3): 22.79 (br. s 2NH); 3.97 (s, 12H, 4MeO); 7.33–
7.77 (m, 16 arm. H); 8.46 (s, 8H (pyrrole)).
7. Hartley, J. A.; Forrow, S. M.; Souhami, R. L. Cancer Res.
1990, 50, 1936.
8. Kadish, K.; Smith, K.; Guilard, R. The porphyrin handbook;
Academic: New York, 2000; Vol. 6. pp 43–131.
9. Rothemund, P. J. Am. Chem. Soc. 1939, 61, 2912.
10. (a) Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Golldmacher, J.;
Assour, J.; Korsakoff, L. J. Org. Chem. 1976, 32, 476.
(b) Longo, F. R.; Finarelli, J. D.; Kim, J. J. Heterocycl. Chem.
1969, 6, 927. (c) Adler, A. R.; Longo, F. R.; Kampas, F.; Kim,
J. J. Inorg. Nucl. Chem. 1970, 32, 2443.
3.1.11. 5,10,15,20-Tetrakis(m-chlorophenyl)porphyrin
(11). Purple crystal; mp .300 8C; yield¼41%; spectro-
scopic data identical to that reported in the literature.12
3.1.12. 5,10,15,20-Tetrakis(m-nitrophenyl)porphyrin
(12). Purple crystal; mp .300 8C; yield¼40%; [Found: C,
66.38; H, 3.27; N, 14.22. C44H26N8O8 requires C, 66.50; H,
3.27; N, 14.10%]; lmax (benzene; log 1): 418 nm (5.72), 480
(3.08), 515 (4.33), 550 (4.04), 591 (4.02), 646 (3.63). dH
(250 MHz, CDCl3): 22.96 (br. s 2NH); 8.13–8.70 (m, 16
arom. H); 8.93 (s, 8H (pyrrole)).
11. (a) Lindsey, J. S.; Hsu, H. C.; Schreiman, I. C. Tetrahedron
Lett. 1986, 27, 4969. (b) Lindsey, J. S.; Schreiman, I. C.; Hsu,
H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem.
1987, 52, 827. (c) Lindsey, J. S.; Wagner, R. W. J. Org. Chem.
1989, 54, 828. (d) Wagner, R. W.; Breakwell, B. V.; Ruffing,
J.; Lindsey, J. S. Tetrahedron Lett. 1991, 32, 1703. (e) Lindsey,
J. S.; MacCrum, K. A.; Tyhonas, J. S.; Chuang, Y.-Y. J. Org.
Chem. 1994, 59, 579. (f) Lee, C.-H.; Lindsey, J. S.
Tetrahedron 1994, 50, 11427. (g) Wagner, R. W.; Johnson,
T. E.; Lindsey, J. S. Tetrahedron 1997, 53, 6755.
(h) Ravikanth, M.; Achim, C.; Tyhonas, J. S.; Mu¨nck, E.;
Lindsey, J. S. J. Porphyrins Phthalocyanines 1997, 1, 385.
(i) Li, F.; Yang, K.; Tyhonas, J. S.; MacCrum, K. A.; Lindsey,
J. S. Tetrahedron 1997, 53, 12339. (j) Geier, G. R.; Lindsey,
J. S. J. Porphyrins Phthalocyanines 2002, 6, 159.
3.1.13. 5,10,15,20-Tetrakis(o-methylphenyl)porphyrin
(13). Purple crystal; mp .300 8C; yield¼40%; spectro-
scopic data identical to that reported in the literature.19b
3.1.14. 5,10,15,20-Tetrakis(o-chlorophenyl)porphyrin
(14). Purple crystal; mp .300 8C; yield¼35%; spectro-
scopic data identical to that reported in the literature.19b
3.1.15. 5,10,15,20-Tetrakis(o-nitrophenyl)porphyrin
(15). Purple crystal; mp .300 8C; yield¼27%; [Found: C,
66.53; H, 3.41; N, 14.06. C44H26N8O8 requires C, 66.50; H,
3.27; N, 14.10%]; lmax (benzene; log 1): 422 nm (5.72), 518
(3.99), 550 (3.85), 588 (3.66), 650 (3.36). dH (250 MHz,
CDCl3): 22.95 (br. s 2NH); 7.54–8.27 (m, 16 arom. H);
8.64 (s, 8H (pyrrole)).
12. Johnstone, R. A.; Nunes, M. L.; Pereira, M. M.; Gonsalves,
M. R.; Serra, A. C. Heterocycles 1996, 43, 1423.
13. Sharghi, H.; Hassani Nejad, A. R. J. Chem. Res. (S) 2003, 87.
14. Fischer, H.; Friendrich, H.; Lamatsch, W.; Morgenroth, K.
Liebigs Ann. Chem. 1928, 466, 147.
15. (a) Arsenault, G. P.; Bullock, E.; MacDonald, S. F. J. Am.
Chem. Soc. 1960, 82, 4384. (b) Wallace, D. M.; Leung, S. H.;
Senge, M. O.; Smith, K. M. J. Org. Chem. 1993, 58, 7245.
16. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun.
1994, 2069.
3.1.16. 5,10,15,20-Tetramesitylporphyrin (16). Purple
crystal; mp .300 8C; yield¼25%; spectroscopic data
identical to that reported in the literature.11c
17. Rocha Gonsalves, A. M.; Varejao, J. M. M. J. Heterocycl.
Chem. 1991, 28, 635.
18. Geier, G. R.; Cirigh, Y.; Li, F.; Haynes, D. M.; Lindsey, J. S.
Org. Lett. 2000, 2, 1745.
Acknowledgements
19. (a) Shinoda, T.; Izumi, Y.; Onaka, M. J. Chem. Soc., Chem.
Commun. 1995, 1801. (b) Onaka, M.; Shinoda, T.; Izumi, Y.;
Nolen, E. Tetrahedron Lett. 1993, 34, 2625. (c) Laszlo, P.;
Luchetti, J. Chem. Lett. 1993, 449.
We would like to acknowledge the support of this work
by Shiraz University Research Council and Professor
N. Iranpoor for his helpful comments.