Bicyclization of aza-compounds by positive halide ions. I. Cyclic amines

Abstract

Cyclic amines are oxidized to the bicyclic compounds by electrochemical oxidation. The presence of halide ions is found necessary for the reaction to proceed and to produce any bicyclic products. It is postulated that a positive halide species, X(+), is produced electrochemically and stabilized under the specific reaction conditions. The X(+) ion forms a complex with the parent cyclic amine which decomposes to the bicyclic product and HX. An analogy between the Hofer–Moest reaction to produce C(+) and this reaction to produce X(+) is postulated