Volume 38, Issue 19 pp. 2919-2923
Communication

Isoporphycene: The Fourth Constitutional Isomer of Porphyrin with an N4 Core—Occurrence of E/Z Isomerism

Emanuel Vogel

Emanuel Vogel

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

Search for more papers by this author
Peter Scholz

Peter Scholz

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

Search for more papers by this author
Ralf Demuth

Ralf Demuth

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

Search for more papers by this author
Christoph Erben

Christoph Erben

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

Search for more papers by this author
Martin Bröring

Martin Bröring

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

Search for more papers by this author
Hans Schmickler

Hans Schmickler

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

Search for more papers by this author
Johann Lex

Johann Lex

Institut für Organische Chemie der Universität, Greinstrasse 4, D-50939 Köln (Germany), Fax: (+49) 221-470-5057

Search for more papers by this author
Georg Hohlneicher

Georg Hohlneicher

Institut für Physikalische Chemie der Universität, Luxemburger Strasse 116, D-50939 Köln (Germany), Fax: (+49) 221-470-5144

Search for more papers by this author
Dominik Bremm

Dominik Bremm

Institut für Physikalische Chemie der Universität, Luxemburger Strasse 116, D-50939 Köln (Germany), Fax: (+49) 221-470-5144

Search for more papers by this author
Yun-Dong Wu

Yun-Dong Wu

Department of Chemistry, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong (China)

Search for more papers by this author

Abstract

Liberation of the ligand from the nickel complex 1 obtained by template synthesis yielded isoporphycene (as the octaethyl derivative 2), the first constitutional isomer of porphyrin with an N4 core for which E/Z isomerism is involved: Compound 2 is present as the E isomer, which is in rapid, presumably acid-catalyzed equilibrium with a small amount (2 %) of the Z isomer. The remaining unknown constitutional isomers of porphyrin are considerably higher in energy than the already rather labile isoporphycene, so that the latter should mark the border of existence for this type of structural variant of porphyrin.

The full text of this article hosted at iucr.org is unavailable due to technical difficulties.