Synthesis of Adamantane Derivatives. XIX. Aluminum Chloride-Catalyzed Reactions of N-Chloro-1-Adamantylamine Derivatives

Abstract The chemical behavior of 1-adamantylnitrenium ion seems to be not known much compared to 1-adamantylcarbinyl cation,2 though one example of the rearrangement of 1-adamantylnitrenium ion to 4-azahomoacamantyl ion has been reported recently by Kovacic et al in the reaction of 1-M,N-dichloroaminoadamantane with aluminum chloride.3 From our interest in the reactivity and rearrangement aptitude of 1-adamantylnitrenium ion, we investigated the reactions of various N-substituted N-chloro-1-adamantylamine derivatives with aluminum chloride. This communication deals with the preliminary results which indicated that the reactions of 1-adamantylnitrenium ion are much affected by the N-substituents and also by the solvents used.