Systematic Studies on the Synthesis, Structures, and Properties of Aromatic Compounds Containing Heavier Group 14 Elements

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There has been no stable, neutral heteraaromatic compounds containing heavier group 14 elements, and their structures and properties have been revealed yet. In this Project, we studied on the synthesis of new type of heteraaromatic compounds containing a heavier group 14 element by taking advantage of an effective steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), which is developed by us, and elucidated their structures and properties. Based on these results, we estimated the aromaticity of these compounds, systematically.We succeeded in the synthesis and isolation of the first stable silabenzene, 1-silanaphthalene, 2-silanaphthalene, 9-silaanthracene, germabenzene, and 2-germanaphthalene as stable crystals by taking advantage of Tbt group. The X-ray structural analyses, spectral data on NMR, UV/vis, and Raman spectroscopy, and theoretical calculations indicated that all these compounds are aromatic compounds as aromaticity these compounds showed the high reactivities to H_2O, alcohols, olefins, alkynes, ketones, and nitrile oxides and underwent ready addition of these reagents to the Si=C or Ge=C double-bond.We think that the new knowledge obtained in this project lays the foundations of the chemistry of heteraaromatic compounds containing heavier group 14 elements. We expect that novel properties and functions of heteraaromatic compounds containing heavier group 14 elements will be revealed on the basis of these results, showing the potential applicability and these chemistry will be applied to the synthesis of novel functional compounds and novel catalysis.