Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

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

  • 34 Accesses


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.

This is a preview of subscription content, log in to check access.

Literature cited

  1. 1.

    G. R. Krow, Tetrahedron,37, No. 7, 1283 (1981).

  2. 2.

    P. Brun, R. Furstoss, P. Teissier, W. Tubiana, and B. Waegell, C.R. Acad. Sci., Paris,269, No. 6, 427 (1969).

  3. 3.

    R. W. Gottingham, J. Org. Chem.,25, 1473 (1960).

  4. 4.

    J. Soloducho and A. Zabza, Pol. J. Chem.,53, No. 5, 1497 (1979).

  5. 5.

    H. K. Hall, J. Org. Chem.,28, 3213 (1963).

  6. 6.

    A. Zabza, C. Wawrzenczyk, and H. Kuchynski, Bull. Acad. Pol. Sci., Ser. Sci. Chem., No. 22, 855 (1974).

  7. 7.

    H. Erdtman and S. Thoren, Acta Chem. Scand.,24, No. 1, p. 87 (1970).

  8. 8.

    A. Daniel and A. A. Pavia, Tetrahedron Lett., 1145 (1967).

  9. 9.

    H. Paulsen, K. Todt, and H. Ripperger, Chem. Ber.,101, 1145 (1968).

  10. 10.

    N. G. Kozlov and T. I. Pekhk, Zh. Org. Khim.,18, No. 5, 1118 (1982).

Download references

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.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

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).

Download citation


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