Sv. Chapyshev et T. Ibata, CINE-SUBSTITUTION IN REACTIONS OF DICHLORO-1,4-BENZOQUINONES WITH PYRROLIDINE, Russian chemical bulletin, 45(11), 1996, pp. 2561-2568
Products of cine-substitution are formed in reactions of 2,5- and 2,6-
dichloro-1,l-benzoquinones with pyrrolidine. The main reason for amina
tion of chloroquinones by pyrrolidine via the mechanism of cine-substi
tution is the high basicity of this amine. A high degree of localizati
on of the pi-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
.