Synthesis of 7-azabicyclo[2.2.1]heptane derivatives via bridgehead radicals

This report shows the versatility and synthetic potential of 7-azabicyclo[2.2.1]heptane-1-carboxylic acid (Ahc) to obtain several bridgehead 1-substituted-7-azabicyclo[2.2.1]heptane derivatives, including halogen derivatives, via bridgehead radical reactions, proving the existence of the bridgehead radical in 7-azabicyclo[2.2.1]heptane systems. Moreover, we have obtained the interesting compound N-benzoyl-7-azabicyclo[2.2.1]heptane, a precursor of epibatidine. (C) 2002 Elsevier Science Ltd. All rights reserved.