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The synthesis of macrocyclic ether‐esters, thioether‐esters, and ether‐thiolesters with the oxalyl moiety
Author(s) -
Fore Paul F.,
Bradshaw Jerald S.,
Nielsen Steven F.
Publication year - 1978
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.5570150217
Subject(s) - chemistry , thioether , oxalyl chloride , moiety , ether , decane , chloride , stereochemistry , organic chemistry , medicinal chemistry
A new series of macrocyclic polyether‐diesler compounds ( 3‐12 ) have been prepared by treating various oligoethylene glyeols or mercaplans with oxalyl chloride. The compounds prepared were: 1,4,7,10,13‐pentaoxacyclopentadecane‐2,3‐dione ( 3 ), 1,4,7,1 3‐tetraoxa‐10‐thiacyclopenta‐decane‐2,3‐dione ( 4 ), 1,4,10‐lrioxa‐7,13‐dithiacyclopenladecane‐2,3‐dione ( 5 ), 1,4,7,10,13,16‐hexaoxacyclooctadecane‐2,3‐dione ( 6 ), 1,4,7,10,13, 16‐hexaoxacyclooctadecane‐2,3,11,12‐tetra‐one ( 7 ), 1,4,10,13‐tetraoxa‐7,16‐dithiacyclooctadecane‐2,3,11,12‐tetraone ( 8 ), 7,16‐dioxa‐1,4, 10,13‐letralhiacyclooctadecane‐2,3,11,12‐tctraone ( 9 ), 1,4,7,10,13,16‐hexathiacyclooctadecane‐2,3,11,12‐tetraone ( 10 ), 1,4,7,10,13,16,19‐heptaoxacyclohencicosane‐2,3‐dione (11), and 1,4,7, 10,13,16,19,22‐octaoxacyclolelracosane‐2,3,14,15‐letraone ( 12 ).