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Synthesis of substituted 14‐crown‐4 compounds
Author(s) -
Czech Bronislaw P.,
Zazulak Wolodymyr,
Kumar Anand,
Olsher Uriel,
Feinberg Hadar,
Cohen Shmuel,
Shoham Gil,
Dalley N. Kent,
Bartsch Richard A.
Publication year - 1992
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.5570290604
Subject(s) - chemistry , crown (dentistry) , thiocyanate , lithium (medication) , tetra , medicinal chemistry , solid state , stereochemistry , organic chemistry , medicine , dentistry , endocrinology
Seventeen new substituted 14‐crown‐4 derivatives 3‐10, 35‐40, 42, 45 and 46 are described. A series of nine compounds 2‐10 with two, three or four substituents in the 6‐ and/or 13‐positions was synthesized in good yields from the appropriate diols and ditosylates using improved cyclization conditions. The solid state structures of 6,6,13,13‐tetra(benzyloxymethyl)‐14‐crown‐4 ( 8 ) and lithium thiocyanate complexes of trans ‐ and cis ‐6,13‐bis(spiro‐2,2‐dichlorocyclopropyl)‐14‐crown‐4 ( 45 ) and ( 46 ), respectively, have been determined.