Novel Podands and Macrocycles with Diacetal (Tetraoxadecalin) Cores: Synthesis, Structure, Stereochemistry and Cation Inclusion

Sarah Abramson, Eli Ashkenazi, Klaus Frische, Israel Goldberg, Larisa Golender, Moshe Greenwald, N. Gabriel Lemcoff, Ravit Madar, Sarah Weinman, Benzion Fuchs

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)6071-6082
Number of pages12
JournalChemistry - A European Journal
Volume9
Issue number24
DOIs
StatePublished - 15 Dec 2003

Keywords

  • Cations
  • Diacetals
  • Diazacrowns
  • Host-guest systems
  • Macroheterocycles
  • Tetraoxadecalins

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