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Chemistry of Natural Compounds

, Volume 29, Issue 3, pp 306–308 | Cite as

Selective conversion of the oximes of pinocamphone and isopinocamphone into bicyclic lactams

  • S. S. Koval'skaya
  • N. G. Kozlov
  • G. V. Kalechits
Article
  • 39 Downloads

Abstract

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.

Keywords

Oxime Lactam Spin Coupling Constant Beckmann Rearrangement Selective Conversion 

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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • S. S. Koval'skaya
  • N. G. Kozlov
  • G. V. Kalechits

There are no affiliations available

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