Rates of Formation of Iminium Ions from Acetone and Monoprotonated 2-pyrrolidine
The kinetics of the reaction of 2-pyrrolidine (1) with acetone has been studied by experiments in which the reversibly formed iminium ion is captured irreversibly by hydroxylamine.From experiments over the pH range 8.5-10.6 rate constants for iminium ion formation from 1 and 1-H+ were obtained.These rate constants were smaller than the corresponding rate constant for pyrrolidine, but the value for 1-H+ was large enough to show that the intermediate carbinolamine was undergoing internal acid-catalyzed dehydration to give the iminium ion.
Hine, Jack,Evangelista, Ramon A.
p. 3890 - 3892
(2007/10/02)
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