1,4-Diamino-and 1,4-dibutylamino-anthraquinones: reduction and/or deprotonation-initiated elimination of the butyl groups in dipolar aprotic media

Abstract

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.