Bicyclization of aza-compounds by positive halide ions. II: Lactams and some related cyclizations

Anodic oxidation of lactams in the presence of halide ions produced excellent yields of bicyclic compounds with reactants having rings in the range of eight to ten atoms (C7 to C9). Smaller rings did not react to form bicyclic products and larger rings gave reduced yields. Attempts were made to cyclize non-cyclic amides and to bicyclize cycloheptyl and cyclooctyl acetamide with limited success.