Dynamic path bifurcation in the Beckmann reaction: Support from kinetic analyses

Y Yamamoto, H Hasegawa…

Index: Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4652 - 4660

Full Text: HTML

Citation Number: 31

Abstract

The reactions of oximes to amides, known as the Beckmann rearrangement, may undergo fragmentation to form carbocations+ nitriles when the migrating groups have reasonable stability as cations. The reactions of oxime sulfonates of 1-substituted-phenyl-2-propanone derivatives (7-X) and related substrates (8-X, 9a-X) in aqueous CH3CN gave both rearrangement products (amides) and fragmentation products (alcohols), the ratio of ...