REACTIONS OF AMINES. VI. SYNTHESIS OF α-AMINO KETONES AND ACIDS FROM IMINO DERIVATIVES^1,2

The Rearrangement of Ketoxime O-Sulfonates to Amino Ketones (The Neber Rearrangement)

“…Catalytic hydrogenation in the presence of water gave 2,4-dinitrophenylacetone. 4. Catalytic hydrogenation in the presence of acetic anhydride gave an acetylated vinyl amine.…”

“…The first stage of this reaction has been shown (1,4) to involve dehydrochlorination of the dichloroalkyl amine (XX) to the N-chloroketimine (XXI). The second stage, conversion to the -amino ketone (XXIV), was considered to proceed by a mechanism similar to that described by Hatch and Cram for the Neber rearrangement, the intermediate being the azirine (XXII) or the methoxyethylenimine (XXIII).…”