Calixpphyrins: Novel macrocycles at the intersection between porphyrins and calixphyrroles

Angewandte Chemie - International Edition

Volumn 39, Issue 6, 2000, Pages 1055-1058

  Král, Vladimír ^b   Sessler, Jonathan L ^a   Zimmerman, Rebecca S ^a   Seidel, Daniel ^a   Lynch, Vincent ^a   Andrioletti, Bruno ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b CZECH TECHNICAL UNIVERSITY IN PRAGUE   (Czech Republic)

Author keywords

Heterocycles; Macrocycles; N ligands; Porphyrinogens; Porphyrinoids

Indexed keywords

ACETONE; ANION; CATION; LIGAND; MACROCYCLIC COMPOUND; NITRILE; NITROGEN; PORPHYRIN; PORPHYRINOGEN; PYRROLE DERIVATIVE;

ARTICLE; BINDING COMPETITION; CHEMICAL STRUCTURE; OXIDATION; POLYMERIZATION; SYNTHESIS;

EID: 0038319949     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000317)39:6<1055::AID-ANIE1055>3.0.CO;2-O     Document Type: Article

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43. An alternative approach to preparing porphodimethenes and related systems, involving the mixed condensation of an aldehyde, ketone, and pyrrole, was also tested. As expected, such a reaction generates a statistical mixture of possible products.
44. Lewis acids were found to be far less efficacious as catalysts to produce only trace quantities of products.
45. o)), and GoF=1.34 for 416 refined parameters. The tetrameric calixpyrrole lies around a crystallographic two-fold rotation axis. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-134665 and 134666. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
46. A reaction analogous to that of Scheme 1 but employing a bipyrrole, rather than dipyrromethane derivative, produced, inter alia, a cyclotrimer and a cyclotetramer under a variety of reaction conditions. These compounds will be discussed in a subsequent report.
47. For an alternative approach to the synthesis of large bipyrrole-derived calixphyrin analogues, see: M. Michels, L. Zander, J. Wytko, Abstr. 24th Int. Symp. Macrocyc. Chem. (Barcelona), 1999.
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