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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.