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Novel Porphyrinoids, 13. – Synthesis and Electrophilic Substitution of New Partially β‐Unsubstituted [18]Porphyrins
Author(s) -
Franck Burchard,
Krautstrunk Gerhard
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301172
Subject(s) - chemistry , porphyrin , regioselectivity , electrophilic substitution , pyrrole , electrophile , electrophilic aromatic substitution , annulene , ring (chemistry) , stereochemistry , substitution reaction , medicinal chemistry , photochemistry , organic chemistry , catalysis
Three porphyrins 2, 3 , and 4 , related to Hans Fischer's octaethylporphyrin 1 , but with unsubstituted pyrrole β‐positions were synthesized via the biladiene pathway. The ring‐closing reaction to form the porphyrin reveals a conformational control, called helical effect . These new porphyrins made possible an investigation of the regioselectivity of electrophilic aromatic substitutions at the porphyrin perimeter.