THE SNAR REACTION OF 2,3,5,6-TETRACHLORONITROBENZENE WITH DIAMINES UNDER HIGH-PRESSURE - FORMATION OF CYCLIZATION PRODUCTS

The reaction of 2,3,5,6-tetrachloronitrobenzene with ethylenediamine u nder 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 r atio of the products varied depending upon the amount of amine used. O ther diamines, such as 1,4-butanediamine cis-and trans-1,2-cyclohexane diamines, m-xylylenediamine, and o-phenylenediamine, gave similar resu lts. On the other hand, N,N'-dimethylethylenediamine and N,N'-dimethyl -1,3-propanediamine gave cyclization products through successive subst itutions of an ortho-chlorine atom and a nitro group by the two methyl amino groups of a molecule of diamine. N-Methylethylenediamine afforde d 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.