Contracted porphyrins: Octaethylisocorrole

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 23, 1997, Pages 2612-2615

  Vogel, Emanuel ^a   Binsack, Beate ^a   Hellwig, Yvonne ^a   Erben, Christoph ^a   Heger, Andreas ^a   Lex, Johann ^a   Wu, Yun Dong ^b  

^a UNIVERSITY OF COLOGNE   (Germany)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Copper; Isocorrole; McMurry reaction; N ligands; Porphyrinoids

Indexed keywords

EID: 0031573951     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199726121     Document Type: Article

References (33)

1. A. W. Johnson, Pure Appl. Chem. 1971, 28, 195; R. Grigg in The Porphyrins, Vol. II (Ed.: D. Dolphin), Academic Press, New York, 1978, p. 327.
2. A. W. Johnson, Pure Appl. Chem. 1971, 28, 195; R. Grigg in The Porphyrins, Vol. II (Ed.: D. Dolphin), Academic Press, New York, 1978, p. 327.
3. a) A. Eschenmoser, Angew. Chem. 1988, 100, 5; Angew. Chem. Int. Ed. Engl. 1988, 27, 5;
4. a) A. Eschenmoser, Angew. Chem. 1988, 100, 5; Angew. Chem. Int. Ed. Engl. 1988, 27, 5;
5. b) A. I. Scott, ibid. 1993, 105, 1281 and 1993, 32, 1223;
6. b) A. I. Scott, ibid. 1993, 105, 1281 and 1993, 32, 1223;
7. c) F. Blanche, B. Cameron, J. Crouzet, L. Debussche, D. Thibaut, M. Vuilhorgne, F. J. Leeper, A. R. Battersby, ibid. 1995, 107, 421 and 1995, 34, 383;
8. c) F. Blanche, B. Cameron, J. Crouzet, L. Debussche, D. Thibaut, M. Vuilhorgne, F. J. Leeper, A. R. Battersby, ibid. 1995, 107, 421 and 1995, 34, 383;
9. d) B. Kräutler, C. Kratky, ibid. 1996, 108, 179 and 1996, 35, 167.
10. d) B. Kräutler, C. Kratky, ibid. 1996, 108, 179 and 1996, 35, 167.
11. For metal complexes of corroles sec the excellent review by S. Licoccia, R. Paolesse, Struct. Bonding (Berlin) 1995, 84, 71.
12. a) E. Vogel, S. Will, A. Schulze Tilling, L. Neumann, J. Lex, E. Bill, A. X. Trautwein, K. Wieghardt, Angew. Chem. 1994, 106, 771; Angew. Chem. Int. Ed. Engl. 1994, 33, 731;
13. a) E. Vogel, S. Will, A. Schulze Tilling, L. Neumann, J. Lex, E. Bill, A. X. Trautwein, K. Wieghardt, Angew. Chem. 1994, 106, 771; Angew. Chem. Int. Ed. Engl. 1994, 33, 731;
14. b) E. Van Caemelbecke, S. Will, M. Autret, V. A. Adamian, J. Lex, J.-P. Gisselbrecht, M. Gross, E. Vogel, K. M. Kadish, Inorg. Chem. 1996, 35, 184;
15. c) S. Will, J. Lex, E. Vogel, H. Schmickler, J.-P. Gisselbrecht, C. Haubtmann, M. Bernard, M. Gross, Angew. Chem. 1997, 109, 367; Angew: Chem. Int. Ed. Engl. 1997, 36, 357.
16. c) S. Will, J. Lex, E. Vogel, H. Schmickler, J.-P. Gisselbrecht, C. Haubtmann, M. Bernard, M. Gross, Angew. Chem. 1997, 109, 367; Angew: Chem. Int. Ed. Engl. 1997, 36, 357.
17. R. Paolesse, R. K. Pandey, T. P. Forsyth, L. Jaquinod, K. R. Gerzevske, D. J. Nurco, M. O. Senge, S. Licoccia, T. Boschi, K. M. Smith, J. Am. Chem. Soc. 1996, 118, 3869.
18. R. Paolesse, S. Licoccia, G. Bandoli, A. Dolmella, T. Boschi, Inorg. Chem. 1994, 33, 1171.
19. II-octaethylporphycenate displays the (Z) configuration, the free octaethylisoporphycene ligand has an (E) configuration both in solution and in the crystal: E. Vogel, M. Bröring, R. Demuth, C. Erben, P. Scholz, unpublished results.
20. II-octaethylporphycenate displays the (Z) configuration, the free octaethylisoporphycene ligand has an (E) configuration both in solution and in the crystal: E. Vogel, M. Bröring, R. Demuth, C. Erben, P. Scholz, unpublished results.
21. Calculations of the corrole isomers were carried out independently of ourselves by A. Ghosh and K. Jynge. The method used by these authors (LDF) produced relative stabilities for the isomers that correspond qualitatively with those reported here. We thank Prof. A. Ghosh, University of Tromsø (Norway) for sending us his manuscript.
22. S. Will, A. Rahbar, H. Schmickler, J. Lex, E. Vogel, Angew. Chem. 1990, 102, 1434; Angew. Chem. Int. Ed. Engl. 1990, 29, 1390.
23. S. Will, A. Rahbar, H. Schmickler, J. Lex, E. Vogel, Angew. Chem. 1990, 102, 1434; Angew. Chem. Int. Ed. Engl. 1990, 29, 1390.
24. E. Vogel, M. Bröring, C. Erben, R. Demuth, J. Lex, M. Nendel, K. N. Houk, Angew. Chem. 1997, 109, 363; Angew. Chem. Int. Ed. Engl. 1997, 36, 353.
25. E. Vogel, M. Bröring, C. Erben, R. Demuth, J. Lex, M. Nendel, K. N. Houk, Angew. Chem. 1997, 109, 363; Angew. Chem. Int. Ed. Engl. 1997, 36, 353.
26. H. Falk, The Chemistry of Linear Oligopyrroles and Bile Pigments, Springer, Vienna, 1989, p. 115.
27. E. Vogel, P. Koch, X.-L. Hou, J. Lex, M. Lausmann, M. Kisters, M. A. Aukauloo, P. Richard. R. Guilard, Angew: Chem. 1993, 105, 1670; Angew: Chem. Int. Ed. Engl. 1993, 32, 1600.
28. E. Vogel, P. Koch, X.-L. Hou, J. Lex, M. Lausmann, M. Kisters, M. A. Aukauloo, P. Richard. R. Guilard, Angew: Chem. 1993, 105, 1670; Angew: Chem. Int. Ed. Engl. 1993, 32, 1600.
29. III ground state and others in a higher, excited, triplet (paramagnetic) state [4c]. A crystal structure analysis of 10 shows that the aldehyde group is disordered, but it can be definitely stated that the copper isocorrolate ring system is almost planar.
30. Ka radiation λ = 0.71069 Å). The structure was solved by using direct methods and subsequently refined (heavy atoms with anisotropic, H atoms with isotropic temperature factors). The calculations were carried out on a pdp-11/23-plus microcalculator using MoIEN (Enraf-Nonius). The crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100426. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union road, Cambridge, CB21EZ, UK (fax: Int code+ (1223)336-033; e-mail deposit@chemcrys.cam.ac.uk).
31. H. R. Harrison, O. J. R. Hodder, D. Crowfoot Hodgkin, J. Chem. Soc. B 1971, 640.
32. Unpublished experiments with B. Binsack, S. Will, and C. Erben.
33. Iv correlate pendants [4a]. However, due to disordered crystals more precise X-ray crystallographic data on these complexes are not available presently.