Stereochemistry of the [3+2] Cycloaddition of Acrylonitrile to the N-Oxide of 5-Methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1'-cyclohexane]

The 3+2] cycloaddition of acrylonitrile to the N-oxide of 5-methyl-4,5-dihydro-3H-spirobenz-2-azepine-3,1'-cyclohexane] under conditions of both kinetic and thermodynamic control proceeds without regioselectivity or stereoselectivity with the formation of eight isomeric 1-cyano- and 2-cyano-7-methyl-1,2,4,6,7,11b-hexahydro-5H-spiroisoxazolidino3,2-a]benz-2-azepine-5,1'-cyclohexanes], six of which were isolated in an individual state. Their structure and stereochemistry were established by ¹H NMR.