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The synthesis of di‐ and tetramethyl substituted macrocyclic polyether‐diester ligands
Author(s) -
Bradshaw Jerald S.,
Jolley Scott T.
Publication year - 1979
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.5570160614
Subject(s) - chemistry , potassium thiocyanate , triethylene glycol , chloride , pyridine , perchlorate , methylene , ring (chemistry) , medicinal chemistry , thiocyanate , polymer chemistry , organic chemistry , ion
Three series of macrocyclic polyether‐diester ligands have been prepared from dimethyl triethylene glycol ( 20 ), two dimethyl tetraethylene glycols ( 21,23 ), dimethyl pentaethylene glycol ( 22 ) and tetramethyl tetraethylene glycol ( 24 ) and diglycolyl chloride (products 5–9 ), thiadiglycolyl chloride (products 10–14 ) and 2,6‐pyridine dicarbonyl chloride (products 15–19 ). The eighteen‐membered rings ( 6 and 16 ) formed solid potassium thiocyanate complexes. The eighteen‐ and twenty‐one‐membered ring compounds 6–8 and 16–18 complexed with benzylammonium perchlorate in methylene chloride‐ d 2 as shown by significant chemical shift changes in the 1 H nmr spectra.