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.