Catalytic hydrogenation of 12 gave 1, perhydro [OO] paracyclophane: IR v 2920, 1480, 1460 cm-'. The high symmetry of 1 on the NMR time scale is apparent from its two line proton- decoupled I3C NMR spectrum: b 30.2 (4 C, d, J= 130 Hz) and 24.6 ppm (8 C, t, J= 126 Hz). The'H NMR spectrum shows a significant downfield shift for the endo protons, presumably a result of steric cornpre~ sion:~~ 6 2.03 (8 H, br d, J= 9 Hz), 1.95 (4 H, br s), 1.48 ppm (8 H, ...