Tetrahedron p. 1887 - 1892 (1983)
Update date:2022-08-29
Topics:
Kufer, W.
Scheer, H.
The reaction of bilirubins with aromatic diazonium salts in alcoholic solvents leads to an equimolar mixture of two types of products.One is the well-known 9-azopyrromethenone.The other is a yellow product (λmax=420nm) identified as 9-alkoxymethylpyrromethenone, the alkoxy-substituent being derived from the solvent.Thus, reaction of the symmetrically substituted bilirubins IIIα (1c) and XIIIα (1b) in methanol with diazotized sulfanilic acid yields one mole of the azopigments (4b and 4a), respectively, and one mole of the corresponding 9-methoxymethylpyrromethenones (2b and 2a).Bilirubin IXα (1a) consequently yields a mixture of all four products.The two resulting 9-methoxymethylpyrromethenones were separated by chromatography and identified as 2a and 2b.They can react further with the diazonium salts to give the corresponding 9-azopyrromethenones, but the reaction is much slower than that of bilirubin, which explains the observed product distribution.These results are discussed in relation to earlier work.
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