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.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
G. R. Krow, Tetrahedron,37, No. 7, 1283 (1981).
P. Brun, R. Furstoss, P. Teissier, W. Tubiana, and B. Waegell, C.R. Acad. Sci., Paris,269, No. 6, 427 (1969).
R. W. Gottingham, J. Org. Chem.,25, 1473 (1960).
J. Soloducho and A. Zabza, Pol. J. Chem.,53, No. 5, 1497 (1979).
H. K. Hall, J. Org. Chem.,28, 3213 (1963).
A. Zabza, C. Wawrzenczyk, and H. Kuchynski, Bull. Acad. Pol. Sci., Ser. Sci. Chem., No. 22, 855 (1974).
H. Erdtman and S. Thoren, Acta Chem. Scand.,24, No. 1, p. 87 (1970).
A. Daniel and A. A. Pavia, Tetrahedron Lett., 1145 (1967).
H. Paulsen, K. Todt, and H. Ripperger, Chem. Ber.,101, 1145 (1968).
N. G. Kozlov and T. I. Pekhk, Zh. Org. Khim.,18, No. 5, 1118 (1982).
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.
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). https://doi.org/10.1007/BF00629825
- Organic Chemistry
- Sulfuric Acid
- Hydrochloric Acid