The Influence of Substituents on the Hydroxyl-Bearing Carbon in the Aza-Payne Rearrangement of Aziridinemethanols

A new series of α,α-disubstituted aziridinemethanols have been synthesized and their aza-Payne rearrangement reactions were studied. The results show that α,α-disubstituted aziridinemethanols with electron-withdrawing groups accelerate the aza-Payne rearrangement than those with electron-donating groups. All of the rearrangements proceeded through an inversion of configuration at the C-2 carbon.