Cyclic and Macrocyclic Molecules Containing Silicon or Tin – Synthesis of Highly Rigid, Potentially Lewis‐Acidic Cryptands

Highly rigid silicon- and tin-containing macrocyclic and bicyclic cage compounds with diethynylbenzene backbones were synthesized and characterized and their potential as Lewis acids was explored.

Abstract

Herein we report the syntheses of highly rigid silicon- and tin-containing cyclic and bicyclic compounds with unsaturated organic backbones. The syntheses proceed via di-lithiated diethynylbenzene derivatives. The protocols for the known precursor compounds were significantly improved in a two-step one-pot reaction with yields up to 45% by alternating addition of the lithiation reagent and starting material. A total of ten compounds were synthesized and the molecular structure in the solid state was elucidated for six novel compounds. Host-guest-experiments with selected molecules were conducted to investigate on the potential of the complexation of small anions. All compounds were characterized by multinuclear NMR spectroscopy and elemental analyses or mass spectrometry and in most parts by SC-XRD analyses.

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