25975-32-0Relevant articles and documents
Preparation of cyclopropanediol: Novel [2 + 1] cycloaddition reaction of bis(iodozincio)methane with 1,2-diketones [27]
Ukai,Oshima,Matsubara
, p. 12047 - 12048 (2007/10/03)
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Mechanistic Change in Acid-Catalyzed Hydrolysis of Silyl Vinyl Ethers
Novice, Marilyn H.,Seikaly, Hani R.,Seiz, Annette D.,Tidwell, Thomas T.
, p. 5835 - 5838 (2007/10/02)
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.