Monoamine oxidase-catalyzed oxidation of endo,endo-2-amino-6-[(Z)-2'-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate

An 11-step synthesis of endo,endo-2-amino-6-(E)-2'-phenyl]ethenylbicyclo2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed.