Abstract
The conversion of diferrocenylphenylmethanol (5) into the carbocation is general acid catalyzed in H/sub 2/O:CH/sub 3/CN, 1:1 w/w, and ..cap alpha.. = 0.88. The corresponding reaction of tropyl alcohol is also general acid catalyzed, and ..cap alpha.. = 0.71 and 0.90 in water and H/sub 2/O:CH/sub 3/CN, 1:1 w/w, respectively. However, the hydrogen ion catalyzed reactions have inverse solvent kinetic hydrogen isotope effects, and k/sub H20//k/sub D20/ = 0.56 for reaction of 5 in H/sub 2/O(D/sub 2/O):CH/sub 3/CN. 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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