Journal of the American Chemical Society p. 5835 - 5838 (1980)
Update date:2022-09-26
Topics:
Novice, Marilyn H.
Seikaly, Hani R.
Seiz, Annette D.
Tidwell, Thomas T.
tert-Butyldimethylsilyl vinyl ethers t-BuMe2SiOCR=CH2 hydrolyze in 50percent CH3CN - H2O with general and specific acid catalysis and a linear dependence of log kH+ on ?p+(R), indicating that the reaction occurs with rate-determing proton transfer to carbon (the ADE2 mechanism).By contrast the rates of trimethylsilyl vinyl ethers Me3SiOCR=CH2 are not correlated by ?p+(R) but still depend on proton and general acid concentrations.Nucleophilic attack on silicon is implicated in the rate-determing step of the latter compounds, and the possibilities for the details of this process are considered.
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