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Synthesis and properties of a new series of trögerophanes

✍ Scribed by Alhussein A. Ibrahim; Mutsumi Matsumoto; Yuji Miyahara; Kenji Izumi; Masahiko Suenaga; Nobujiro Shimizu; Takahiko Inazu

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
520 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

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.

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