Abstract
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.
Keywords: Aziridinemethanols, aza-Payne rearrangement, inversion of configuration, electron-withdrawing groups, electrondonating groups
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