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Mutual Interconversion of the Chromophoric Systems of Porphyrinogen and Isobacteriochlorin
Author(s) -
Angst Christof,
Kajiwara Masahiro,
Zass Engelbert,
Eschenmoser Albert
Publication year - 1980
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198001401
Subject(s) - tautomer , chemistry , ion , metal ions in aqueous solution , metal , stereochemistry , crystallography , organic chemistry
Reactions of hexahydroporphyrins in the absence of air are strongly influenced by metal ions. Thus the tetrapyrrolic porphyrinogen (1) , R = C 2 H 5 , reacts in the presence of Co 2+ via several steps, including isobacteriochlorins (2) , to give the hemicorrinoid dipyrrolic compounds (3) . These are tautomers of (1) . In the presence of Ni 2+ , (1) form complexes of the new hemicorrinoid‐pyrromethenic system (4). ttct‐(4) and tttt‐(4) were characterized by their spectra and also by X‐ray structure analysis. (The species ttt‐(2), ttt‐(3) , and tttt‐(4) likewise formed are not included in the scheme below.)