SEMMLER • WOLFF - SCHROETER Oxime

SEMMLER WOLFF SCHROETER OximeAromatizatlon Aramatization of cyclohexanone oximes to anilines... 

This reaction was first reported by Semmler in 1892 and subsequently studied by Wolff in 1902 and Schroeter in 1911. It is the rearrangement of an oxime of an a,p unsaturated cyclohexenone (or known as the o, )0-unsaturated cyclohexenyl ketoxime) to an aromatic amine in a mixture of acetic anhydride and acetic acid saturated with HCl or HBr. Therefore, this reaction is generally known as the Semmler-Wolff aromatization," Semmler-Wolff rearrangement, or Semmler-Wolff reaction. Occasionally, it is also referred to as the Semmler-Wolff-Schroeter reaction. It should be pointed out that the Beckmann Rearrangement,and the fragmentation to nitriles often compete with the Semmler-Wolff aromatization. In addition, the Semmler-Wolff aromatization is obstructed by the substituents close to the reaction center. ... 

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