Reactions of 2-methyleneadamantane and 2-benzylideneadamantane with acetyl nitrate

Resumo

The reactions of 2-methylene- and 2-benzylideneadamantane with acetyl nitrate have been studied. In the case of 2-methyleneadamantane, the reaction proceeds via addition of nitronium cation at the double bond followed by stabilization of 2-nitromethyl-2-adamantyl carbocation. In the case of 2-benzylidenadamantane, ortho-substitution at the benzene ring occurred predominantly.