The synthesis of 1-silolyl and 1-germolyl triflates from the corresponding chlorides by salt metathesis reaction is reported. These covalent triflates are ideal starting materials for the preparation of ionic silolyl- and germolyl-imidazolium triflates by their reaction with N-heterocyclic carbenes. Similarily, ionic silolyl- and germolyl-oxophosphonium triflates are obtained by substitution of the triflate group by triethylphosphane oxide EtPO. The analysis of their P NMR chemical shifts according to the Gutmann-Beckett method reveal the high Lewis acidity of the underlying silolyl and germolyl cations. Further analysis of structural and NMR parameters of the silolyl- and germolyl-imidazolium and oxophosphonium triflates indicates that these compounds are covalently bonded silole and germole derivatives with insignificant contributions from silolyl- or germolyl cations. Silolyl and germolyl triflates are however synthetic equivalents of these cations and might serve as a source for electrophilic silolyl and germolyl units.
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http://dx.doi.org/10.1039/d2dt01446g | DOI Listing |
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