Acid-Catalyzed Hydration of α-Cyano and α-Trifluoromethyl Vinyl Ethers. Additivity of Strongly Activating and Strongly Deactivating Substituent Effects

Article abstract of DOI:10.1021/ja00373a030

The reactivities of 1-cyano-1-ethoxyethylene (1) and 1-(trifluoromethyl)-1-ethoxypentene (2) in aqueous H2SO4 and D2SO4 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 logk_H+ = -10.5Σ_p⁺ - 8.92.