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 ...

Related Articles:

One-pot stibine modified Co 2 (CO) 8 catalyzed reductive N-alkylation of primary amides with carbonyl compounds

[Rubio-Perez, Laura; Sharma, Pankaj; Perez-Flores, F. Javier; Velasco, Luis; Arias, J. Luis.; Cabrera, Armando Tetrahedron, 2012 , vol. 68, # 10 p. 2342 - 2348]

Simple, High Yield Preparation of N-Benzylacetamides by Lewis Acid-Catalyseed Reaction of Benzyl Chlorides or Benzyl Methyl Ethers with Acetonitrile

[Kacan; McKillop Synthetic Communications, 1993 , vol. 23, # 15 p. 2185 - 2189]

More Articles...