Transannular cyclisation of cyclo-olefinic N-chloro-amines. Synthesis of azabicyclic compounds

Abstract

N-Chloro-N-methylcyclo-oct-4-enamine and N-chloro-N-methylcyclohept-4-enamine cyclise in the presence of various catalysts and solvents to give 2-substituted, nitrogen-bridged bicyclic compounds. The structures and stereochemistry of these products have been determined; several experiments with the eight-membered N-chloro-amine demonstrating the radical chain nature of the cyclisations are described.