Regarding the structure of [2.2](2,6,2',7')-naphthalenophane-1,11-diene and its conformational mobility

The synthesis of 2.2](2,6,2',7')naphthalenophane -1,11 - diene 4 has been effected by pyrolysis of the bis-sulphoxide 10, in turn prepared by a ring-contraction procedure of the 3.3]dithiacyclophane 7. The diene 4 has been fully characterized by spectroscopic and chemical methods. The variable-temperature ¹H NMR spectra of the diene 4 indicated that the compound undergoes conformational flipping in solution and has a conformational energy barrier ΔG^≠_25°. 14.9 kcal mol^-1 and a coalescence temperature T_c 38° for the internal protons H_c and H_c' (at 100 MHz). These results differ from those previously recorded. A complete assignment of the pmr spectrum of the cyclophane diene 4 at 270 MHz is presented together with the spectrum of the corresponding saturated 2.2]cyclophane 3.