Cine-substitution in reactions of dichloro-1,4-benzoquinones with pyrrolidine

Article abstract of DOI:10.1007/BF01431116

Products of cine-substitution are formed in reactions of 2,5- and 2,6-dichloro-1,4-benzoquinones with pyrrolidine. The main reason for amination of chloroquinones by pyrrolidine via the mechanism of cine-substitution is the high basicity of this amine. A high degree of localization of the π-bond in the molecules of the starting chloroquinones and the strong conjugation of the amino group with the quinone ring in the molecules of the intermediate monoaminoquinones are two other factors that favor an increase in yields of the products of cine-substitution.