36287-93-1Relevant articles and documents
Photochemical Substitution of Amino- and Hydroxy-anthraquinones
Hamilton, Kenneth,Hunter, John A.,Preston, Peter N.,Morley, John O.
, p. 1544 - 1548 (2007/10/02)
Irradiation of 1-aminoanthraquinone with visible light in the presence of an excess of either sodium sulphite or sulphide in 50percent aqueous pyridine gives exclusively sodium 1-aminoanthraquinone-2-sulphonate and -2-thiolate, respectively, in good yield.Under similar conditions with sodium sulphite, 1-methylamino-, 1-amino-4-chloro-, and 1-amino-5-chloro-anthraquinone give the respective sodium 2-sulphonate only, while 2-aminoanthraquinone gives the sodium 3-sulphonate.In contrast, 1-hydroxyanthraquinone gives a mixture of the sodium 2- and 4-sulphonates and disodium 2,4-disulphonates.The different substitution pattern observed for 1-amino- and 1-hydroxy-anthraquinone has been rationalised by application of semi-empirical molecular orbital theory.
