Dearomatization of [2.2]Paracyclophane-Derived N -Sulfonylimines through Cyclopropanation with Sulfur Ylides.

An unprecedented dearomatization of [2.2]paracyclophane-derived cyclic N -sulfonylimines was conducted through cyclopropanation with sulfur ylides, giving a series of dearomative cyclopropanes with good yields. DFT calculations suggested that the dearomatization was attributed to the relatively weak aromaticity of [2.2]paracyclophane derivatives that resulted from the effect of the unique [2.2]paracyclophane skeleton and the electron-withdrawing N -sulfonyl group. Some downstream elaborations of the products were demonstrated.