Synthesis of anti -[1](1,6)Naphthaleno[1](1,6)naphthalenophane by Double Contractive Annulation of [2.2]Paracyclophane.

Two-directional contractive annulation of [2.2]paracyclophane has led to the synthesis of anti -[1](1,6)naphthaleno[1](1,6)naphthalenophane ( 3 ). This [1.1]cyclophane (SE = 56.6 kcal/mol) consists of two bent and twisted naphthalene units with interplanar distances as short as 2.74 Å. Despite the high strain and structural distortion, 3 was found to be unreactive toward potential cycloaddition partners (TCNE, DMAD) and under UV irradiation.