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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 17, Number 6
BKCSDE 17(6)
June 20, 1996 

Facile Syntheses of Modified Tripyrranes and their Application to the Syntheses of Regioisomerically Pure Porphyrin Derivatives
Phil-Yeon Heo, Chang-Hee Lee*
Simple conditions were discovered to afford tripyrranes by reaction of 2,5-bis(α -hydroxymethyl)furan or 2,5-bis(α-hydroxy-α -phenylmethyl)thiophene with excess pyrrole in the presence of acid catalyst. Stepwise synthesis of porphyrins with core-ligand modification and synthesis of meso-tetraarylporphyrins bearing two different substituents in cis orientation have developed as building blocks for the various porphyrin-based model systems. Consequently, 21-thia-23-oxa-10,15-diphenylporphyrin (28), 21-oxa-10,15-diphenylporphyrin (29) and 21-oxa-23-carba-12-aza-10,15-diphenylporphyrin (30) were synthesized by acid-catalyzed [3+1] condensation between tripyrranes and 2,5-bis(α -hydroxymethyl)pyrrole or 2,5-bis(α-hydroxy-α -phenylmethyl)thiophene. The synthetic pathway described here gave regioisomerically pure porphyrins and thus overcame the synthetic problems associated with separation and purification of regioisomeric mixture.
515 - 520
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