Heterocyclization of tropinone oximes and 3-methyl-3-azabicyclo[3.3.1]-nonan-9-one with acetylene in a superbasic medium

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. ©1999 KluwerAcademic/Plenum Publishers.