- STRUCTURE OF THE BORATE COMPLEXES OF α-AMINO AND α-HYDROXY-9,10-ANTHRAQUINONES AND THEIR REACTION WITH AMINES
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It was shown by 13C NMR that a redistribution of the bonds with partial localization of the 1,5- and 1,10-anthraquinonoid structures occurs during the transition from 1,5-diamino(dihydroxy)- and 1-amino(hydroxy)-9,10-anthraquinones respectively to their borate complexes.For this reason the boroacetates and fluoroborates of 1,5-dihydroxyanthraquinonones, 1-aminoanthraquinones, their N-alkyl and N-aryl derivatives, and 1,5-dihydroxyanthraquinone are capable of entering into amination under the influence of aromatic amines with substitution of the hydrogen atom at position 4 under mild conditions with the participation of atmospheric oxygen as oxidizing agent
- Gorelik, M. V.,Shapet'ko, N. N.,Arinich, L. V.,Tsurkan, A. I.,Kukushkina, M. L.
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p. 547 - 556
(2007/10/02)
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- Reactions of 1,5-Dichloroanthrachinone with Nucleophiles
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Reactions of 1,5-dichloroanthraquinone (1) with various nucleophiles were examined to evaluate possibilities for selective substitution. 1-Amino-5-chloroanthraquinone was obtained from 1 by reaction with (a) sodium azide in dimethyl sulfoxide and (b ammonia in the presence of potassium fluoride, but 1 with potassium in ammonia gave 3-chlorobenzoic acid.Conditions were found for preferential substitution in reactions of 1 with (c) 4-toluidine, (d) hexamethylphosphoric triamide, and (e) N-methylformamide.Reagent e is preferred for making 1-chloro-5-(methylamino)anthraquinone, though this compound predominates in mixtures produced when d is used.Potassium hydroxide in 2-ethoxyethanol converts 1 to the corresponding mono- and diethers of 1,5-dihydroxyanthraquinone, while sodium hydrosulfide and 1 give bis(5-chloroanthraquinonyl)sulfide.
- Ruediger, Edward H.,Kaldas, Magdy L.,Ghandi. Sham S.,Fedryna, Cristi,Gibson, Martin S.
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p. 1974 - 1978
(2007/10/02)
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