A Hg(OTf)2 catalyzed intramolecular arene 1,4-addition reaction of N-benzyl donor鈥揳cceptor cyclopropenecarboxamides was developed to synthesize a series of [3.2.2]nonatriene derivatives. This novel reaction is also observed with silver(I) catalysts known to form metal carbene intermediates in competition with the Buchner reaction.