Synthesis and Properties of a New Series of Trögerophanes

Alhussein A. Ibrahim, Mutsumi Matsumoto, Yuji Miyahara, Kenji Izumi, Masahiko Suenaga, Nobujiro Shimizu, Takahiko Inazu

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18 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)209-215
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume35
Issue number1
DOIs
Publication statusPublished - Jan 1 1998

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Ibrahim, A. A., Matsumoto, M., Miyahara, Y., Izumi, K., Suenaga, M., Shimizu, N., & Inazu, T. (1998). Synthesis and Properties of a New Series of Trögerophanes. Journal of Heterocyclic Chemistry, 35(1), 209-215. https://doi.org/10.1002/jhet.5570350139