Abstract
The title mol-ecular salt, C17H30NSi+·C2H5O4S-, belongs to the class of a-amino-silanes and was synthesized by the alkyl-ation of 1-[(benzyl-dimethyl-sil-yl)meth-yl]piperidine using diethyl sulfate. This achiral salt crystallizes in the chiral space group P21. One of the Si-C bonds in the cation is unusually long [1.9075 (12) Å], which correlates with the adjacent quaternary N+ atom and was verified by quantum chemical calculations. In the crystal, the components are linked by weak C-H⋯O hydrogen bonds: a Hirshfeld surface analysis was performed to further investigate these inter-molecular inter-actions and their effects on the crystal packing.
Highlights
Selective bond transformations on silicon compounds for the cleavage of Si—C bonds are of high interest in silicon chemistry (Denmark et al, 2007; Denmark & Liu, 2010)
Our group has focused on using lithium organyls as strong nucleophiles to perform these Si—C transformations on highly substituted silanes (Bauer & Strohmann, 2014)
When strong nucleophiles are used, deprotonation in the benzyl position competes with the selective Si—C bond cleavage of the benzyl group
Summary
Selective bond transformations on silicon compounds for the cleavage of Si—C bonds are of high interest in silicon chemistry (Denmark et al, 2007; Denmark & Liu, 2010). When strong nucleophiles are used, deprotonation in the benzyl position competes with the selective Si—C bond cleavage of the benzyl group For this purpose, the -aminofunctionality seems to play a key role, which could be responsible for the activation of the subsequent Si—C bond cleavage. A selective cleavage of the amino functionality due to the elongated Si—C bond is conceivable (Bent, 1960, 1961; Otte et al, 2017) Structural studies concerning this type of compound should better elucidate the reactivity as well as selectivity of Si—C cleavages of the benzyl-substituted -aminosilanes
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