Addition of sterically hindered organolithium compounds to meso-tetraphenylporphyrin

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1165-1168

  Krattinger, Bénédicte ^a   Callot, Henry J ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOLITHIUM COMPOUND; PORPHYRIN DERIVATIVE; TETRAPHENYLPORPHYRIN;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0032485323     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10792-4     Document Type: Article

References (28)

1. 1. Sugimoto, H. J. Chem. Soc. Dalton Trans. 1982, 1169-1171; Setsune, J.; Ikeda, T.; Iida, T.; Kitao, T. J. Am. Chem. Soc. 1988, 110, 6572-6574; Setsune, J.; Ishimaru, Y.; Kitao, T. Chem. Lett. 1990, 1351-1354; Setsune, J.; Yamaji, H.; Kitao, T. Tetrahedron Lett. 1990, 31, 5057-5060; Setsune, J.; Wada, K.; Higashino, H. Chem. Lett. 1994, 213-216; Segawa, H.; Azumi, R.; Shimidzu, T. J. Am. Chem. Soc. 1992, 114, 7564-7565; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760.
2. 1. Sugimoto, H. J. Chem. Soc. Dalton Trans. 1982, 1169-1171; Setsune, J.; Ikeda, T.; Iida, T.; Kitao, T. J. Am. Chem. Soc. 1988, 110, 6572-6574; Setsune, J.; Ishimaru, Y.; Kitao, T. Chem. Lett. 1990, 1351-1354; Setsune, J.; Yamaji, H.; Kitao, T. Tetrahedron Lett. 1990, 31, 5057-5060; Setsune, J.; Wada, K.; Higashino, H. Chem. Lett. 1994, 213-216; Segawa, H.; Azumi, R.; Shimidzu, T. J. Am. Chem. Soc. 1992, 114, 7564-7565; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760.
3. 1. Sugimoto, H. J. Chem. Soc. Dalton Trans. 1982, 1169-1171; Setsune, J.; Ikeda, T.; Iida, T.; Kitao, T. J. Am. Chem. Soc. 1988, 110, 6572-6574; Setsune, J.; Ishimaru, Y.; Kitao, T. Chem. Lett. 1990, 1351-1354; Setsune, J.; Yamaji, H.; Kitao, T. Tetrahedron Lett. 1990, 31, 5057-5060; Setsune, J.; Wada, K.; Higashino, H. Chem. Lett. 1994, 213-216; Segawa, H.; Azumi, R.; Shimidzu, T. J. Am. Chem. Soc. 1992, 114, 7564-7565; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760.
4. 1. Sugimoto, H. J. Chem. Soc. Dalton Trans. 1982, 1169-1171; Setsune, J.; Ikeda, T.; Iida, T.; Kitao, T. J. Am. Chem. Soc. 1988, 110, 6572-6574; Setsune, J.; Ishimaru, Y.; Kitao, T. Chem. Lett. 1990, 1351-1354; Setsune, J.; Yamaji, H.; Kitao, T. Tetrahedron Lett. 1990, 31, 5057-5060; Setsune, J.; Wada, K.; Higashino, H. Chem. Lett. 1994, 213-216; Segawa, H.; Azumi, R.; Shimidzu, T. J. Am. Chem. Soc. 1992, 114, 7564-7565; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760.
5. 1. Sugimoto, H. J. Chem. Soc. Dalton Trans. 1982, 1169-1171; Setsune, J.; Ikeda, T.; Iida, T.; Kitao, T. J. Am. Chem. Soc. 1988, 110, 6572-6574; Setsune, J.; Ishimaru, Y.; Kitao, T. Chem. Lett. 1990, 1351-1354; Setsune, J.; Yamaji, H.; Kitao, T. Tetrahedron Lett. 1990, 31, 5057-5060; Setsune, J.; Wada, K.; Higashino, H. Chem. Lett. 1994, 213-216; Segawa, H.; Azumi, R.; Shimidzu, T. J. Am. Chem. Soc. 1992, 114, 7564-7565; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760.
6. 1. Sugimoto, H. J. Chem. Soc. Dalton Trans. 1982, 1169-1171; Setsune, J.; Ikeda, T.; Iida, T.; Kitao, T. J. Am. Chem. Soc. 1988, 110, 6572-6574; Setsune, J.; Ishimaru, Y.; Kitao, T. Chem. Lett. 1990, 1351-1354; Setsune, J.; Yamaji, H.; Kitao, T. Tetrahedron Lett. 1990, 31, 5057-5060; Setsune, J.; Wada, K.; Higashino, H. Chem. Lett. 1994, 213-216; Segawa, H.; Azumi, R.; Shimidzu, T. J. Am. Chem. Soc. 1992, 114, 7564-7565; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760.
7. 1. Sugimoto, H. J. Chem. Soc. Dalton Trans. 1982, 1169-1171; Setsune, J.; Ikeda, T.; Iida, T.; Kitao, T. J. Am. Chem. Soc. 1988, 110, 6572-6574; Setsune, J.; Ishimaru, Y.; Kitao, T. Chem. Lett. 1990, 1351-1354; Setsune, J.; Yamaji, H.; Kitao, T. Tetrahedron Lett. 1990, 31, 5057-5060; Setsune, J.; Wada, K.; Higashino, H. Chem. Lett. 1994, 213-216; Segawa, H.; Azumi, R.; Shimidzu, T. J. Am. Chem. Soc. 1992, 114, 7564-7565; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760.
8. 2. Krattinger, B.; Callot, H.J. Chem. Commun. 1996, 1341-1342.
9. 3. Krattinger, B.; Callot, H.J. Tetrahedron Lett. 1996, 37, 7699-7702.
10. 4. Arnold, J.; Dawson, D.Y.; Hoffman, C.G. J. Am. Chem. Soc. 1993, 115, 2707-271; Brand, H.; Capriotti, J.A.; Arnold, J. Inorg. Chem. 1994, 33, 4334-4337; Tsuchiya, S. J. Chem. Soc. Chem. Comm. 1992, 1475-1477.
11. 4. Arnold, J.; Dawson, D.Y.; Hoffman, C.G. J. Am. Chem. Soc. 1993, 115, 2707-271; Brand, H.; Capriotti, J.A.; Arnold, J. Inorg. Chem. 1994, 33, 4334-4337; Tsuchiya, S. J. Chem. Soc. Chem. Comm. 1992, 1475-1477.
12. 4. Arnold, J.; Dawson, D.Y.; Hoffman, C.G. J. Am. Chem. Soc. 1993, 115, 2707-271; Brand, H.; Capriotti, J.A.; Arnold, J. Inorg. Chem. 1994, 33, 4334-4337; Tsuchiya, S. J. Chem. Soc. Chem. Comm. 1992, 1475-1477.
13. 5. Typical recent articles: Crossley, M.J.; King, L.G. J. Org. Chem. 1993, 58, 4370-437; Crossley, M.J.; Harding, M.M.; Tansey, C.W. J. Org. Chem. 1994, 59, 4433-4437; Jaquinod, L.; Gros, C.; Olmstead, M.M.; Antolovich, M.; Smith, K.M. Chem. Commun. 1996, 1475-1476; Jaquinod, L.; Gros, C.; Khoury, R.; Smith, K.M. Chem. Commun. 1996, 2581-2582; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760; DiMagno, S.G.; Lin, V.S.Y.; Therien, M.J. J. Org. Chem. 1993, 58, 5983-5993; LeCours, S.M.; Guan, H.W.; DiMagno, S.G.; Wang, C.H.; Therien, M.J. J. Am. Chem. Soc. 1996, 118, 1497-1503.
14. 5. Typical recent articles: Crossley, M.J.; King, L.G. J. Org. Chem. 1993, 58, 4370-437; Crossley, M.J.; Harding, M.M.; Tansey, C.W. J. Org. Chem. 1994, 59, 4433-4437; Jaquinod, L.; Gros, C.; Olmstead, M.M.; Antolovich, M.; Smith, K.M. Chem. Commun. 1996, 1475-1476; Jaquinod, L.; Gros, C.; Khoury, R.; Smith, K.M. Chem. Commun. 1996, 2581-2582; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760; DiMagno, S.G.; Lin, V.S.Y.; Therien, M.J. J. Org. Chem. 1993, 58, 5983-5993; LeCours, S.M.; Guan, H.W.; DiMagno, S.G.; Wang, C.H.; Therien, M.J. J. Am. Chem. Soc. 1996, 118, 1497-1503.
15. 5. Typical recent articles: Crossley, M.J.; King, L.G. J. Org. Chem. 1993, 58, 4370-437; Crossley, M.J.; Harding, M.M.; Tansey, C.W. J. Org. Chem. 1994, 59, 4433-4437; Jaquinod, L.; Gros, C.; Olmstead, M.M.; Antolovich, M.; Smith, K.M. Chem. Commun. 1996, 1475-1476; Jaquinod, L.; Gros, C.; Khoury, R.; Smith, K.M. Chem. Commun. 1996, 2581-2582; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760; DiMagno, S.G.; Lin, V.S.Y.; Therien, M.J. J. Org. Chem. 1993, 58, 5983-5993; LeCours, S.M.; Guan, H.W.; DiMagno, S.G.; Wang, C.H.; Therien, M.J. J. Am. Chem. Soc. 1996, 118, 1497-1503.
16. 5. Typical recent articles: Crossley, M.J.; King, L.G. J. Org. Chem. 1993, 58, 4370-437; Crossley, M.J.; Harding, M.M.; Tansey, C.W. J. Org. Chem. 1994, 59, 4433-4437; Jaquinod, L.; Gros, C.; Olmstead, M.M.; Antolovich, M.; Smith, K.M. Chem. Commun. 1996, 1475-1476; Jaquinod, L.; Gros, C.; Khoury, R.; Smith, K.M. Chem. Commun. 1996, 2581-2582; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760; DiMagno, S.G.; Lin, V.S.Y.; Therien, M.J. J. Org. Chem. 1993, 58, 5983-5993; LeCours, S.M.; Guan, H.W.; DiMagno, S.G.; Wang, C.H.; Therien, M.J. J. Am. Chem. Soc. 1996, 118, 1497-1503.
17. 5. Typical recent articles: Crossley, M.J.; King, L.G. J. Org. Chem. 1993, 58, 4370-437; Crossley, M.J.; Harding, M.M.; Tansey, C.W. J. Org. Chem. 1994, 59, 4433-4437; Jaquinod, L.; Gros, C.; Olmstead, M.M.; Antolovich, M.; Smith, K.M. Chem. Commun. 1996, 1475-1476; Jaquinod, L.; Gros, C.; Khoury, R.; Smith, K.M. Chem. Commun. 1996, 2581-2582; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760; DiMagno, S.G.; Lin, V.S.Y.; Therien, M.J. J. Org. Chem. 1993, 58, 5983-5993; LeCours, S.M.; Guan, H.W.; DiMagno, S.G.; Wang, C.H.; Therien, M.J. J. Am. Chem. Soc. 1996, 118, 1497-1503.
18. 5. Typical recent articles: Crossley, M.J.; King, L.G. J. Org. Chem. 1993, 58, 4370-437; Crossley, M.J.; Harding, M.M.; Tansey, C.W. J. Org. Chem. 1994, 59, 4433-4437; Jaquinod, L.; Gros, C.; Olmstead, M.M.; Antolovich, M.; Smith, K.M. Chem. Commun. 1996, 1475-1476; Jaquinod, L.; Gros, C.; Khoury, R.; Smith, K.M. Chem. Commun. 1996, 2581-2582; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760; DiMagno, S.G.; Lin, V.S.Y.; Therien, M.J. J. Org. Chem. 1993, 58, 5983-5993; LeCours, S.M.; Guan, H.W.; DiMagno, S.G.; Wang, C.H.; Therien, M.J. J. Am. Chem. Soc. 1996, 118, 1497-1503.
19. 5. Typical recent articles: Crossley, M.J.; King, L.G. J. Org. Chem. 1993, 58, 4370-437; Crossley, M.J.; Harding, M.M.; Tansey, C.W. J. Org. Chem. 1994, 59, 4433-4437; Jaquinod, L.; Gros, C.; Olmstead, M.M.; Antolovich, M.; Smith, K.M. Chem. Commun. 1996, 1475-1476; Jaquinod, L.; Gros, C.; Khoury, R.; Smith, K.M. Chem. Commun. 1996, 2581-2582; Jiang, X.; Nurco, D.J.; Smith, K.M. Chem. Commun. 1996, 1759-1760; DiMagno, S.G.; Lin, V.S.Y.; Therien, M.J. J. Org. Chem. 1993, 58, 5983-5993; LeCours, S.M.; Guan, H.W.; DiMagno, S.G.; Wang, C.H.; Therien, M.J. J. Am. Chem. Soc. 1996, 118, 1497-1503.
20. 6. Ema, T.; Senge, M.O.; Nelson, N.Y.; Ogoshi, H.; Smith, K.M. Angew. Chem. Int. Ed. Engl. 1994, 33, 1879-1881.
21. 3, resp. maj and min).
22. 3): 8.47 (2, 2H, pyrrole), 8.35 (s, 2H, pyrrole), 8.02 (d, 2H, pyrrole), 7.3-7.9 (m, 2OH, mesophenyl), 5.02 (s, 2H, 2-H + 3-H), 0.55 (slightly broadened s, 18, t-Bu), -0.6 (broad signal, 2H, N-H).
23. D > 3000.
24. w(F) = 0.067. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.
25. 11. Botulinski, A.; Buchler, J.W.; Abbes, N.B.; Scheidt, W.R. Liebigs Ann., 1987, 305-309.
26. 12. Botulinski, A.; Buchler, J.W.; Lay, K.L.; Stoppa, H. Liebigs Ann., 1984, 1259-1269. Buchler, J.W.; Lay, K.L.; Lee, Y.J.; Scheidt, W.R. Angew. Chem. Int. Ed. Engl. 1982, 21, 432-433 and references cited.
27. 12. Botulinski, A.; Buchler, J.W.; Lay, K.L.; Stoppa, H. Liebigs Ann., 1984, 1259-1269. Buchler, J.W.; Lay, K.L.; Lee, Y.J.; Scheidt, W.R. Angew. Chem. Int. Ed. Engl. 1982, 21, 432-433 and references cited.
28. 13. Crossley, M.J.; Hambley, T.W.; King, L.G. Bull. Soc. Chim. Fr., 1996, 133, 735-742.