Synthesis and properties of a new series of trögerophanes | Zendy

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

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Synthesis and properties of a new series of trögerophanes

Author(s) -

Ibrahim Alhussein A.,

Matsumoto Mutsumi,

Miyahara Yuji,

Izumi Kenji,

Suenaga Masahiko,

Shimizu Nobujiro,

Inazu Takahiko

Publication year - 1998

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570350139

Subject(s) - chemistry , yield (engineering) , hydrochloric acid , thiocyanate , lithium (medication) , series (stratigraphy) , ethanol , base (topology) , stereochemistry , organic chemistry , medicine , paleontology , materials science , metallurgy , biology , endocrinology , mathematical analysis , mathematics

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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