Abstract Bridgehead primary amines in the bicyclic and tricyclic category have served as important intermediates in organic synthesis. When transformed into azo compounds, they can be used as a source of bridgehead free radicals.1 These amines also serve as precursors of azides which, when subjected to photolysis, lead to bridge-head imines (limits of Bredt's rule).2 The N,N-dichloro derivatives undergo skeleton rearrangements in the presence of strong Lewis acids resulting in ring expansion with incorporation of nitrogen.3 Bicyclic and tricyclic bridgehead amines and their derivatives exhibit a wide spectrum of pharmacodynamical properties.4