Interaction of N-trimethylsilylimidazole with electrophilic trimethylsilyl compounds. Part 2. Some exchange reactions involving bistrimethylsilylimidazolium salts
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 2,p. 227-231
- https://doi.org/10.1039/p29860000227
Abstract
The dynamic and equilibrium properties of bistrimethylsilimidazolium salts (1) have been investigated by n.m.r. spectroscopy. The salts (1) are highly susceptible to nucleophilic attack. The exchange reactions of (1) with electrophilic silanes (TMSX) have also been studied, in one example by the dynamic n.m.r. method of total line-shape analysis. The rate of the exchange reaction decrease (X = Cl > Br > CF3SO3 > I,CIO4). The equilibrium constants for formation of (1) were found to decrease in the order Me3SiClO4 > Me3SiOSO2CF3 > Me3Sil > Me3SiBr > Me3SiCl. These results are shown to be consistent with silylation mechanisms involving silylated nucleophiles as intermediates.Keywords
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