On the Mechanism of the Carbodesilylation of 4‐ or 5‐Substituted 2‐(Trimethylsilyl)pyridines An “ylide mechanism” is proposed for the carbodesilylation of 2‐(trimethylsilyl)pyridines with benzaldehyde. In contrast, 3‐and 4‐(trimethylsilyl)pyridines, react only in the presence of a base catalyst via pyridyl anions with electrophiles. The rates of the uncatalyzed carbodesilylation reactions of 4‐substituted 2‐(trimethylsilyl)pyridines 2 with benzaldehyde correlate very well with the resonance parameters of the substituents ρRO, whereas the rates of 5‐substituted 2‐(trimethylsilyl)pyridines 7 correlate with the inductive substituent parameters ρI in the Taft equation. This is to our knowledge the first direct determination of the resonance parameters ρRO.
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Effenberger et al. (1992) studied this question.
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