Selective conversion of the oximes of pinocamphone and isopinocamphone into bicyclic lactams
- 38 Downloads
A method is proposed for the selective conversion of oximes of terpene ketones of the pinane (2,6,6-trimethylbicyclo[3.1.1]heptane) series into the corresponding bicyclic lactams which consists in the action on these oximes of sulfuric acid in a weak nucleophile — a nitrile. The fact that the interaction takes place through the stage of formation of N-acylamidines — products of the nucleophilic stabilization of the intermediate carbocations — permits the rearrangement of the latter and the formation of monocyclic products to be avoided, which makes it possible to obtain in good yields bicyclic lactams, the synthesis of which by other methods is problematical.
KeywordsOxime Lactam Spin Coupling Constant Beckmann Rearrangement Selective Conversion
Unable to display preview. Download preview PDF.
- 3.J. Soloducho and A. Zabza,Pol. J. Chem. 53 No. 5, 1497–1510 (1979).Google Scholar
- 5.A. Zabza, C. Warwzenczyk, and H. Kuchinski,Bull. Acad. Pol. Sci. Ser. Sci. Chem. 22 No. 10, 855–862 (1974).Google Scholar
- 7.S. S. Koval'skaya, H. G. Kozlov, and S. V. Shavyrin,Khim. Prir. Soedin., No. 1, 29–32 (1991).Google Scholar
- 8.G. V. Kalechits and N. G. Kozlov, USSR Inventor's Certificate No. 1162783,Byull. Izobret., No. 23, 17 (1985).Google Scholar