The Journal of Organic Chemistry

Rates of formation of iminium ions from acetone and monoprotonated 2-[(dimethylamino) methyl] pyrrolidine

J Hine, RA Evangelista

Index: Hine, Jack; Evangelista, Ramon A. Journal of Organic Chemistry, 1980 , vol. 45, # 19 p. 3890 - 3892

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Citation Number: 2

Abstract

Results Lithium aluminum hydride reduction of N, N-di-methyl-5-oxo-2- pyrrolidinecarboxamide gave 1, which has also been prepared by reduction of the N, N- dimethylamide of pr~ line.~ Its thermodynamic pK, values in water at 35" C were found to be 9.82 and 5.77. Equilibrium constants for iminium ion formation from acetone and secondary amines in aqueous solution are so small that it is not practical to follow the reactions ...