Tetrahedron

Formation of α-iminoketones and α-diimines versus Favorskii rearrangement products from the reaction of α, α′-dibromoketones and primary amines

N De Kimpe, L D'Hondt, L Mones

Index: De Kimpe, Norbert; D'Hondt, Luc; Mones, Luc Tetrahedron, 1992 , vol. 48, # 15 p. 3183 - 3208

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Citation Number: 29

Abstract

The reaction of aliphatic acyclic α, α′-dibromoketones with primary amines gave rise to α- iminoketones and α-diimines. Both reaction products could be selectively obtained under appropriate reaction conditions. Sterically hindered α, α-dibromoketones did not react with primary amines, although, under forcing conditions the Favorskii rearrangement could be induced. In aqueous methanol, α, α′-dibromoketones reacted with primary amines to ...