AI Article Synopsis
- Ketones are important organic compounds due to their carbon-oxygen double bonds, but heavy ketones with E=O bonds (where E is Si, Ge, Sn, or Pb) have been difficult to isolate because they tend to polymerize.
- Researchers have successfully isolated a stable monomeric germanium ketone (Eind)(2)Ge=O by using bulky protecting groups to prevent polymerization, resulting in a planar tricoordinate germanium atom.
- The study indicates that the Ge=O double bond in this compound is highly polarized and can adopt a charge-separated form, leading to unique reactivities, such as its ability to spontaneously trap CO(2) gas.
Article Abstract
The carbon-oxygen double bond of ketones (R(2)C=O) makes them among the most important organic compounds, but their homologues, heavy ketones with an E=O double bond (E = Si, Ge, Sn or Pb), had not been isolated as stable compounds. Their unavailability as monomeric molecules is ascribed to their high tendency for intermolecular oligomerization or polymerization via opening of the E=O double bond. Can such an intermolecular process be inhibited by bulky protecting groups? We now report that it can, with the first isolation of a monomeric germanium ketone analogue (Eind)(2)Ge=O (Eind = 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl), stabilized by appropriately designed bulky Eind groups, with a planar tricoordinate germanium atom. Computational studies and chemical reactions suggest the Ge=O double bond is highly polarized with a contribution of a charge-separated form (Eind)(2)Ge(+)-O(-). The germanone thus exhibits unique reactivities that are not observed with ordinary ketones, including the spontaneous trapping of CO(2) gas to provide a cyclic addition product.
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