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Oxidative Pyrrole Exchange and meso Pyrrylation – Unexpected Reactions of Open‐Chain Tetrapyrrolic 2,2′‐Bidipyrrins
Author(s) -
Bröring Martin,
Link Stephan,
Cordes Meike,
Brandt Carsten D.
Publication year - 2007
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200600268
Subject(s) - pyrrole , chemistry , tetrapyrrole , metalation , ring (chemistry) , medicinal chemistry , ligand (biochemistry) , nickel , chelation , polymer chemistry , stereochemistry , photochemistry , organic chemistry , biochemistry , receptor , enzyme
A new hydrogen terminated 2,2′‐bidipyrrin ligand was prepared from a bipyrrole dialdehyde and 3,4‐diethylpyrrole by a POCl 3 induced condensation and isolated as the nickel(II) chelate. Unexpectedly a side reaction occured when base‐deficient and aerobic conditions were chosen in the metalation step. This side reaction led to a novel pentapyrrolic nickel(II) complex with one externally bound pyrrole ring. Further studies showed that the reactions of 2,2′‐bidipyrrins with 3,4‐diethyl‐ or 2,3,4‐trimethylpyrrole and an oxidant resulted in a stepwise exchange of the terminal pyrrole moieties and, in the former case, the introduction of one additional pyrrole ring into one of the two meso positions of the open‐chain tetrapyrrole.