62956-46-1Relevant articles and documents
1,4-Diamino- and 1,4-Dibutylamino-anthraquinones: Reduction and/or Deprotonation-initiated Elimination of the Butyl Groups in Dipolar Aprotic Media
Anne, Agnes
, p. 311 - 318 (2007/10/02)
The standard redox potentials of the one- and two-electron reductions of the title compounds have been determined.The deprotonated form of the dibutylamino compound underwent a base-initiated elimination of the butyl groups and the basicity of the radical anion resulting from one-electron reduction was sufficient to provoke the same type of cleavage through an initial father-son reaction.A multi-step mechanism is proposed for the elimination on the basis of the identification of intermediates.
A new Synthesis of 1-Amino-4-butylaminoanthraquinone from 1-Aminoanthraquinone Promoted by Metal Ions
Yoshida, Katsuhira,Matsuoka, Masaru,Yamashita, Yoshio,Kitao, Teijiro
, p. 2552 - 2554 (2007/10/02)
In the presence of some metal ions and atmospheric oxygen, 1-aminoanthraquinone (1) reacts readily with butylamine to give 1-amino-4-butylaminoanthraquinone(2a), along with a small amount of 1,4-diaminoanthraquinone, which is produced by the dealkylation of 2a.The activity of the metal ions decreased in the following order: Co(II) >> Ni(II) above Cu(II) above Al(III).The reaction is remarkably affected by the substitution of an alkyl group into the amino group of 1, the addition of a chelating agent, the counter anion of metal ions, and the reaction temperature.By the use of cobalt(II) chloride, the reaction proceeds most smoothly at about 30 deg C.Both anthraquinone and 2-aminoanthraquinone show no sign of the reaction under the same conditions.A possible mechanism involving the formation of a metal complex, followed by the nucleophilic attack of amine at the 4-position and the oxidative abstraction of the hydride anion by atmospheric oxygen is proposed.
