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Novel Podands and Macrocycles with Diacetal (Tetraoxadecalin) Cores: Synthesis, Structure, Stereochemistry and Cation Inclusion
Author(s) -
Abramson Sarah,
Ashkenazi Eli,
Frische Klaus,
Goldberg Israel,
Golender Larisa,
Greenwald Moshe,
Lemcoff N. Gabriel,
Madar Ravit,
Weinman Sarah,
Fuchs Benzion
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200304999
Subject(s) - cryptand , chemistry , stereochemistry , tetra , alkyl , inclusion (mineral) , polymer chemistry , crystallography , ion , medicinal chemistry , organic chemistry , mineralogy
Abstract A series of functionalized 2,6‐dialkyl‐ cis ‐1,3,5,7‐tetraoxadecalin podands ( 3 – 10 , alkyl = hydroxy‐, mesyloxy‐, halo‐, azido‐ and aminomethyl and ‐ethyl) were prepared, characterized, and used as precursors for a new and interesting class of macrocycles and cryptands ( 12 – 21 ), with the aim to use these as host–guest inclusion systems. Extensive spectroscopic work was performed, structural endorsement was obtained from X‐ray diffraction analyses and further insight into the structures was obtained from theoretical/computational studies. A number of macrocycles in the series exhibited good complexation with alkaline‐earth metal ions.