Stereoisomeric 2,3-Butanediamines, 3-Amino-2-butanols and 2,3-Dimethylethyleneimines; Stereochemistry of the Opening and Closing of the Imine Ring

Abstract

The configurations of the following compounds have been established; the meso-, d- and l-2,3-butanediamines, meso-, d- and l-2,3-dimethylethyleneimines (2,3-dimethylaziridines), and the d- and l-erythro- and d- and l-threo-3-amino-2-butanols. It has been shown that one Walden inversion is associated with a number of ring openings and closing, viz. (1) opening of the oxide ring of 2,3-epoxybutane with ammonia; (2) opening of the imine ring of 2,3-dimethylethyleneimine with ammonia; (3) opening of the same ring wiith water, and (4) closing of the same ring. The reduction of dimethylglyoxime can be accomplished with Raney aluminum-nickel alloy and aqueous base to yield a mixture of dl- and meso-2,3-butanediamine along with some 3-amino-2-butanol. © 1952, American Chemical Society. All rights reserved.