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Novel biphasic synthesis of porphyrin

✍ Scribed by Paul E. Ellis Jr; Wayne A. Langdale


Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
28 KB
Volume
01
Category
Article
ISSN
1088-4246

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✦ Synopsis


An unusual synthesis of porphyrin has been developed using a novel biphasic solvent system. Under optimized conditions reproducible yields of pure porphyrin of over 15% can be easily obtained in about two hours from the acid-catalysed condensation of 2-hydroxymethylpyrrole in a solvent consisting of water and an immiscible ketone. Important variables of the reaction have been studied to improve the yield and characterize the limitations of the reaction.


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The Ο€-extended porphyrins 11a -c with a Ξ» max = 644, 643 and 639 nm were synthesized by an acid catalysed reaction of the dipyrrolylmethane 10 with different aldehydes followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-quinone (DDQ). In a second approach, 10 was decarboxylated to yield 12, whic