Acid catalyzed hydration of. alpha.-cyano and. alpha.-(trifluoromethyl) vinyl ethers. Additivity of strongly activating and strongly deactivating substituent effects

AD Allen, F Shahidi, TT Tidwell

Index: Allen, Annette D.; Shahidi,, Fereidoon; Tidwell, Thomas T. Journal of the American Chemical Society, 1982 , vol. 104, # 9 p. 2516 - 2518

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Citation Number: 17

Abstract

Abstract: The reactivities of 1-cyano-1-ethoxyethene (1) and 1-(trifluoromethy1)-1- ethoxypentene (2) in aqueous H2S04 and D2S04 have been measured. The kinetics and products establish the mechanism of these reactions as rate-limiting protonation on the double bond. The observed rates are predicted with surprising accuracy by the previously introduced correlation log kH+=-10.5~ 0~'-8.92.

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