Novel podands and macrocycles with diacetal (tetraoxadecalin) cores: synthesis, structure, stereochemistry and cation inclusion.
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.
Abramson
Sarah
S
School of Chemistry (Raymond and Beverly Sackler Faculty of Exact Sciences), Tel-Aviv University, Ramat-Aviv, 69978 Tel-Aviv, Israel.
Ashkenazi
Eli
E
Frische
Klaus
K
Goldberg
Israel
I
Golender
Larisa
L
Greenwald
Moshe
M
Lemcoff
N Gabriel
NG
Madar
Ravit
R
Weinman
Sarah
S
Fuchs
Benzion
B
D000080:Acetals / Q000737:chemistry*; D002412:Cations / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008673:Metals, Alkaline Earth / Q000737:chemistry; D008958:Models, Molecular; D009281:Naphthalenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D045568:Tetraoxanes / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
D000080:Acetals; D002412:Cations; D043844:Crown Ethers; D006576:Heterocyclic Compounds, 4 or More Rings; D008673:Metals, Alkaline Earth; D009281:Naphthalenes; D045568:Tetraoxanes; C007229:decalin