Journal of the American Chemical Society p. 3855 - 3858 (1981)
Update date:2022-08-18
Topics:
Bunton, Clifford A.
Davoudazedeh, Faegh
Watts, William E.
The conversion of diferrocenylphenylmethanol (5) into its carbocation is general acid catalyzed in H2O:CH3CN, 1:1 w/w, and α = 0.88.The corresponding reaction of tropyl alcohol is also general acid catalyzed, and α = 0.71 and 0.90 in water and H2O:CH3CN, 1:1 w/w, respectively.However, the hydrogen ion catalyzed reactions have inverse solvent kinetic hydrogen isotope effects, and kH2O/kD2O = 0.56 for reaction of 5 in H2O(D2O):CH3CN.Consideration of the equilibrium constants for alcohol protonation suggests that acid-catalyzed conversion of alcohol into carbocation should go from stepwise to concerted as the stability of the carbocation is increased.
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