PORPHYRINS. 38. REACTION OF PORPHYRINS CONTAINING HYDROXY(ALKOXY)ETHYL OR ALKOXYMETHYL SUBSTITUENTS WITH NUCLEOPHILES IN THE PRESENCE OF ZINC ACETATE. A NOVEL, PROMISING METHOD FOR THE MODIFICATION OF PORPHYRINS ON THE PERIPHERY OF THE MACROCYCLE

Abstract

Porphyrins which contain 1-hydroxy(alkoxy)ethyl or alkoxymethyl substituents on the periphery of the macrocycle (i.e. formally able to yield "benzyl type" carbocations) react with nucleophiles (4- tert -butylphenol or the β-diketones acetylacetone, benzoylacetone, dibenzoylmethane, or 4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione) in the presence of excess zinc acetate. They give high yields of the corresponding addition products, which are the zinc complexes of porphyrins with a 1-(4- tert -butylphenoxy)ethyl substituent or with substituents containing β-diketone residues. Authors: G. V. Ponomarev, G. V. Kirillova, and D. V. Yashunsky. English Translation in Chemistry of Heterocyclic Compounds , 2000, 36 (9), pp 1044-1053 http://link.springer.com/article/10.1023/A%3A1002729830997