Journal of Organic Chemistry p. 3890 - 3892 (1980)
Update date:2022-08-12
Topics:
Hine, Jack
Evangelista, Ramon A.
The kinetics of the reaction of 2-<(dimethylamino)methyl>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.
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