Synthesis and properties of a new series of trögerophanes

A new series of macrocyclic compounds with one or two Troger 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.

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