Synthesis and properties of a new series of trögerophanes

Abstract

Abstract A new series of macrocyclic compounds with one or two Tröger base skeletons has been synthesized by condensing mono‐, di‐, tri‐, and teraethyleneglycol bis ( p ‐aminophenoxy) ethers with formalin in the presence of concentrated hydrochloric acid in ethanol at room temperature for 13 days. This simple one‐step cyclization provided 19 in remarkably high yield (46%) and 17, 18 , and 20 in yields reflecting the strain of the rings and statistical factors. Complexation with lithium thiocyanate was observed for 20 , the structure of which was elucidated by X‐ray crystallography.