Trialkylsilyl(germanyl)propynals show a lower triple bond polarization compared with their carbon analogs because of the electron acceptor effects of the R substituents and the aldehyde group. This increases the inertness of the C≡C bond towards nucleophiles (RSH, R2NH) and lowers the regioselectivity of dipolar attack. Lowering the relative basicity of the substituted propynals decreases the integrated intensity of the C=0 absorption band and shifts the δ17O signal to low field.
|Number of pages||4|
|Journal||Bulletin of the Academy of Sciences of the USSR Division of Chemical Science|
|State||Published - 1 Feb 1988|