The attempted synthesis of nitrogen-containing analogues of [10]paracyclophane

Abstract

A [10]paracyclophane in which –NH– or –NTs– replace the 2′,9′–CH₂-groups of the “para” bridge was the anticipated product of the acyloin condensation of the appropriate bisamino-esters, but elimination and not cyclisation occurred. From the NN′-ditoluene-p-sulphonate of the ester the similar derivative of 1,4-bisaminomethylbenzene was obtained. The preparation of bisamino-esters is described.