HETEROCYCLIZATION OF TROPINONE OXIMES AND 3-METHYL-3-AZABICYCLO[3.3.1]-NONAN-9-ONE WITH ACETYLENE IN A SUPERBASIC MEDIUM

Abstract

Tropinone oxime reacts with acetylene in superbasic medium to form ordinary products of heterocyclization. The oxime of 3-methyl-3-azabicyclo[3.3.1]nonan-9-one does not undergo heterocyclization due to the impossibility of a [3,3]-sigmatropic rearrangement of its vinyl ether.

Authors: A. V. Varlamov, L. G. Voskresenskii, T. N. Borisova, A. I. Chernyshev, and A. N. Levov.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (5), pp 613-616

http://link.springer.com/article/10.1007/BF02324648