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• W1966295561 abstract "A new synthesis of hydroxyporphyrins is reported. The method involves nucleophilic displacement of a nitro group using the sodium salt of E-benzaldoxime and is a general process allowing the synthesis of both β-hydroxyporphyrins and meso-hydroxyporphyrins. Activation of the porphyrin system towards nucleophilic attack is achieved by complexation of the macrocycle with the relatively electronegative nickel(II) or copper(II) ions. Thus, treatment of either the copper(II) or the nickel(II) chelates of 2-nitro-5, 10,15,20-tetraphenylporphyrin with the sodium salt of E-benzaldoxime gave the corresponding 2-hydroxyporphyrin in high yield. Similar treatment of the copper(II) or the nickel(II) chelates of 5-nitro-2, 3,7,8,12,13,17,18-octaethylporphyrin gave the corresponding 5-hydroxyporphyrin, again in high yield. These reactions show that metallo-nitroporphyrins display similar electrophilic properties to much simpler nitro-arene systems. The nickel(II) 5-hydroxyporphyrin 10 was cleanly demetallated on treatment with concentrated sulfuric acid to give the corresponding free-base oxophlorin thereby greatly increasing the general utility of the hydroxylation methodology. Conversion of (5-methoxy-15-nitro-2,3,7,8,12,13,17,18-octaethylporphyrinato) nickel(II) 16 into (5-acetoxy-15-methoxy-2,3,7,8,12,13,17,18-octaethyl-porphyrinato) nickel(II) 18 established that the reaction mechanism involves regiospecific replacement (i.e., ipso-substitution) of the nitro group by the oxygen nucleophile." @default.
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• W1966295561 date "1987-01-01" @default.
• W1966295561 modified "2023-09-23" @default.
• W1966295561 title "A new and highly efficient synthesis of hydroxyporphyrins" @default.
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• W1966295561 doi "https://doi.org/10.1016/s0040-4020(01)86899-x" @default.
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