Mechanistic change in acid-catalyzed hydrolysis of silyl vinyl ethers

MH Novice, HR Seikaly, AD Seiz…

Index: Novice, Marilyn H.; Seikaly, Hani R.; Seiz, Annette D.; Tidwell, Thomas T. Journal of the American Chemical Society, 1980 , vol. 102, # 18 p. 5835 - 5838

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Citation Number: 18

Abstract

Abstract: tert-Butyldimethylsilyl vinyl ethers t-BuMe2SiOCR= CH2 hydrolyze in 50% CH3CN- H20 with general and specific acid catalysis and a linear dependence of log kH+ on upt (R), indicating that the reaction occurs with rate-determining proton transfer to carbon (the AdE2 mechanism). By contrast the rates of trimethylsilyl vinyl ethers Me3SiOCR= CH2 are not correlated by upt (R) but still depend on proton and general acid concentrations. ...