The nature and composition of the Ritter reaction products of 1-[(1E)-3-bromoprop-1-en-1-yl]-adamantane and 1-(3-bromoprop-1-en-2-yl]adamantane are largely determined by the substrate structure, electrophilic medium, and reaction conditions. Possible reaction paths leading to both conventional Ritter reaction products and heterocyclization or skeletal rearrangement products (homoadamantane gamma-sultones) are discussed.