Abstract
A number of benzylsilanes have been synthesised and characterised, and the structural features of certain of these compounds are such that the CSi bond is constrained to varying degrees to the nodal plane of the aromatic system. The proton-decoupled, natural-abundance 13C NMR spectra of these compounds have been obtained and essentially completely assigned on the basis of signal intensities, chemical shifts, selective deuteration and (in some cases) the magnitudes of 13C-19F coupling constants. Comparison of 13C chemical shifts of carbons formally para to the silylmethyl group (CH2Si) in the bicyclic silatetralins and -indanes with the corresponding carbon shifts in the carbon analogues, indicates suppression of the electron-donating effect of the CH2Si group, when the optimum alignment for interaction of the CSi σ-bond and the π-system is prevented. Effects related to strain and special influences operating on the chemical shifts of carbon bearing fluorine, render interpretation for some compounds less straight-forward.
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