Semmler-Wolff Reaction

Semmler-Wolff Reaction

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  • General Characteristics

The synthesis of anilines from the corresponding cyclohexenone oximes is known as the Semmler-Wolff reaction. Due to the competing Beckmann rearrangement, yields tend to be low under classical conditions.

  • General References

  • Semmler, W. Ber. 1892, 25, 3352.
  • Wolff, L. Liebigs Ann. Chem. 1902, 322, 351.
  • Reaction Mechanism


  • Examples

A modified mothod using a palladium catalyst was developed to improve yields.[1] semmler_wolff_2

The synthesis of meta-substituted anilines.[2] semmler_wolff_3

An application to the synthesis of penitrem D.[3] semmler_wolff_5

  •  Experimental Procedure

  • Experimental Tips

  • References

  1. Hong, W. P.; Iosub, A. V.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 13664. doi:10.1021/ja4073172
  2. Kelly, T. R.; Chandrakumar, N. S.; Saha, J. K. J. Org. Chem. 1989, 54, 980. DOI: 10.1021/jo00265a049
  3. Smith, A. B., III; Kanoh, N.; Ishiyama, H.; Minakawa, N.; Rainier, J. D.; Hartz, R. A.; Cho, Y. S.; Cui, H.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 8228. DOI: 10.1021/ja034842k
  • Related Reactions

ベックマン転位 (Beckmann Rearrangement)

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