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Beckmann rearrangement of the E isomer of cis-4,6,6-trimethylbicyclo[3.1.1]-heptan-2-one oxime

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Abstract

The individual E isomer of 4,6,6-trimethylbicyclo[3.1.1]heptan-2-one oxime has been obtained, and its transformations under the conditions of acid catalysis have been studied. The action of sulfuric acid on a solution of the oxime in acetonitrile leads to the selective formation of 5,7,7-trimethyl-2-azabicyclo[4.1.1]octan-3-one, while the action of hydrochloric acid with heating gives 4-isopropyl-3-methylaniline.

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Additional information

Institute of Physical Organic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 29–32, January–February, 1991.

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Koval'skaya, S.S., Kozlov, N.G. & Shavyrin, S.V. Beckmann rearrangement of the E isomer of cis-4,6,6-trimethylbicyclo[3.1.1]-heptan-2-one oxime. Chem Nat Compd 27, 24–27 (1991). https://doi.org/10.1007/BF00629825

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Keywords

  • Organic Chemistry
  • Acetonitrile
  • Sulfuric Acid
  • Hydrochloric Acid
  • Oxime