New porphyrinoid diimines by cyclization of 1,9-bis(5-formylpyrrol-2- yl)dipyrrins with arene-1,2-diamines and hydrazines

Synthesis

Volumn , Issue 4, 1999, Pages 565-567

  Seggewies, Stephan ^a   Schönemeier, Thomas ^a   Breitmaier, Eberhard ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

'expanded texaphyrins'; 22 aromaticity; Dipyrrins; NMR; Porphyrinoid azines; Porphyrinoid diimines; Triaza 22 annulenes

Indexed keywords

HYDRALAZINE; PORPHYRIN DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DECOMPOSITION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0344527756     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3453     Document Type: Article

References (13)

1. Drews, A.; Schönemeier, T.; Seggewies, S.; Breitmaier, E. Synthesis 1998, 749.
2. Vogel, E.; Balci, M.; Pramod, K.; Koch, P.; Lex, J.; Ermer, O. Angew. Chem. 1987, 99, 909; Angew. Chem., Int. Ed. Engl. 1987, 26, 928; this work also includes a brief experimental description of the preparation of 4,4′-dipropyl-2,2′-bipyrrole. A detailed procedure is given in: Johnson, M. R.; Slebodnick, C.; Ibers, J. A. J. Porphyrins and Phthalocyanines 1997, 1, 87.
3. Vogel, E.; Balci, M.; Pramod, K.; Koch, P.; Lex, J.; Ermer, O. Angew. Chem. 1987, 99, 909; Angew. Chem., Int. Ed. Engl. 1987, 26, 928; this work also includes a brief experimental description of the preparation of 4,4′-dipropyl-2,2′-bipyrrole. A detailed procedure is given in: Johnson, M. R.; Slebodnick, C.; Ibers, J. A. J. Porphyrins and Phthalocyanines 1997, 1, 87.
4. Vogel, E.; Balci, M.; Pramod, K.; Koch, P.; Lex, J.; Ermer, O. Angew. Chem. 1987, 99, 909; Angew. Chem., Int. Ed. Engl. 1987, 26, 928; this work also includes a brief experimental description of the preparation of 4,4′-dipropyl-2,2′-bipyrrole. A detailed procedure is given in: Johnson, M. R.; Slebodnick, C.; Ibers, J. A. J. Porphyrins and Phthalocyanines 1997, 1, 87.
5. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1979, 59, 183. Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68. Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661. Vogel, E.; Koch, P.; Hou, X.-L.; Lex, J.; Lausmann, M.; Kisters, M.; Aukauloo, M. A.; Richard, P.; Guilard, R. Angew. Chem. 1993, 105, 1670; Angew. Chem., Int. Ed. Engl. 1993, 32, 1600. Vogel, E.; Bröring, M.; Erben, C.; Demuth, R.; Lex, J.; Nendel, M.; Houk, K. N. Angew. Chem. 1997, 109, 363; Angew. Chem., Int. Ed. Engl. 1997, 36, 353.
6. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1979, 59, 183. Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68. Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661. Vogel, E.; Koch, P.; Hou, X.-L.; Lex, J.; Lausmann, M.; Kisters, M.; Aukauloo, M. A.; Richard, P.; Guilard, R. Angew. Chem. 1993, 105, 1670; Angew. Chem., Int. Ed. Engl. 1993, 32, 1600. Vogel, E.; Bröring, M.; Erben, C.; Demuth, R.; Lex, J.; Nendel, M.; Houk, K. N. Angew. Chem. 1997, 109, 363; Angew. Chem., Int. Ed. Engl. 1997, 36, 353.
7. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1979, 59, 183. Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68. Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661. Vogel, E.; Koch, P.; Hou, X.-L.; Lex, J.; Lausmann, M.; Kisters, M.; Aukauloo, M. A.; Richard, P.; Guilard, R. Angew. Chem. 1993, 105, 1670; Angew. Chem., Int. Ed. Engl. 1993, 32, 1600. Vogel, E.; Bröring, M.; Erben, C.; Demuth, R.; Lex, J.; Nendel, M.; Houk, K. N. Angew. Chem. 1997, 109, 363; Angew. Chem., Int. Ed. Engl. 1997, 36, 353.
8. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1979, 59, 183. Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68. Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661. Vogel, E.; Koch, P.; Hou, X.-L.; Lex, J.; Lausmann, M.; Kisters, M.; Aukauloo, M. A.; Richard, P.; Guilard, R. Angew. Chem. 1993, 105, 1670; Angew. Chem., Int. Ed. Engl. 1993, 32, 1600. Vogel, E.; Bröring, M.; Erben, C.; Demuth, R.; Lex, J.; Nendel, M.; Houk, K. N. Angew. Chem. 1997, 109, 363; Angew. Chem., Int. Ed. Engl. 1997, 36, 353.
9. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1979, 59, 183. Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68. Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661. Vogel, E.; Koch, P.; Hou, X.-L.; Lex, J.; Lausmann, M.; Kisters, M.; Aukauloo, M. A.; Richard, P.; Guilard, R. Angew. Chem. 1993, 105, 1670; Angew. Chem., Int. Ed. Engl. 1993, 32, 1600. Vogel, E.; Bröring, M.; Erben, C.; Demuth, R.; Lex, J.; Nendel, M.; Houk, K. N. Angew. Chem. 1997, 109, 363; Angew. Chem., Int. Ed. Engl. 1997, 36, 353.
10. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1979, 59, 183. Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68. Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661. Vogel, E.; Koch, P.; Hou, X.-L.; Lex, J.; Lausmann, M.; Kisters, M.; Aukauloo, M. A.; Richard, P.; Guilard, R. Angew. Chem. 1993, 105, 1670; Angew. Chem., Int. Ed. Engl. 1993, 32, 1600. Vogel, E.; Bröring, M.; Erben, C.; Demuth, R.; Lex, J.; Nendel, M.; Houk, K. N. Angew. Chem. 1997, 109, 363; Angew. Chem., Int. Ed. Engl. 1997, 36, 353.
11. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1979, 59, 183. Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68. Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661. Vogel, E.; Koch, P.; Hou, X.-L.; Lex, J.; Lausmann, M.; Kisters, M.; Aukauloo, M. A.; Richard, P.; Guilard, R. Angew. Chem. 1993, 105, 1670; Angew. Chem., Int. Ed. Engl. 1993, 32, 1600. Vogel, E.; Bröring, M.; Erben, C.; Demuth, R.; Lex, J.; Nendel, M.; Houk, K. N. Angew. Chem. 1997, 109, 363; Angew. Chem., Int. Ed. Engl. 1997, 36, 353.
12. Schönemeier, T. Dissertation, University of Bonn, 1998.
13. Seggewies, S. Dissertation, in preparation, University of Bonn.