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Conjugated macrocycles related to the porphyrins. Part 3 . Acid catalyzed condensations of thiophenecarboxaldehydes with a dipyrrylmethane
Author(s) -
Armiger Yoek Lin SeeTow,
Lash Timothy D.
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290240
Subject(s) - porphyrin , chemistry , conjugated system , condensation , catalysis , condensation reaction , trace (psycholinguistics) , trace amounts , organic chemistry , combinatorial chemistry , polymer chemistry , photochemistry , polymer , linguistics , physics , medicine , philosophy , alternative medicine , pathology , thermodynamics
Abstract MacDonald condensation of a dipyrrylmethanedicarboxylic acid 3b with 2,2′‐dithienylmethane‐5,5′‐dicarboxaldehyde (2b) failed to give the expected dithiophene porphyrin analog 1b. However, oxidation of the reaction mixtures with DDQ gave trace amounts of porphyrin‐like materials. Model studies indicate that these fractions are meso ‐dithienylporphyrins. The synthesis of three related α,γ‐disubstituted porphyrins is described.