T. Ibata, Xinzhuo Zou, T. Demura
Nov 1, 1995
Citations
0
Influential Citations
4
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The reaction of 2,3,5,6-tetrachloronitrobenzene with ethylenediamine under high pressure gave mainly a 1 : 1-product and a bridged 2 : 1-product by the substitution of a nitro group and/or an o-chlorine atom. The ratio of the products varied depending upon the amount of amine used. Other diamines, such as 1,4-butanediamine cis-and trans-1,2-cyclohexanediamines, m-xylylenediamine, and o-phenylenediamine, gave similar results. On the other hand, N,N′-dimethylethylenediamine and N,N′-dimethyl-1,3-propanediamine gave cyclization products through successive substitutions of an ortho-chlorine atom and a nitro group by the two methylamino groups of a molecule of diamine. N-Methylethylenediamine afforded a 1 : 1-product through the substitution of a nitro group by a primary amino group together with a cyclic 1 : 1-product through substitutions of an o-chlorine atom and a nitro group by secondary and primary amino groups, respectively.