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Updated: May 15, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
β-Elimination of an Aziridine to an Allylic Amine: A Mechanistic Study
Kathleen M Morgan1, Garry Brown, Monique A Pichon
1Department of Chemistry, Xavier University of Louisiana, 1 Drexel Drive, New Orleans LA 70125, USA.
Abstract:
The base-induced rearrangement of aziridines has been examined using a combination of calculations and experiment. The calculations show that the substituent on nitrogen is a critical feature that greatly affects the favorability of both α-deprotonation, and β-elimination to form an allylic amine. Experiments were carried out to determine whether E2-like rearrangement to the allylic amine with lithium diisopropyl amide (LDA) is possible. N-Tosyl aziridines were found to deprotonate on the tosyl group, preventing further reaction. A variety of N-benzenesulfonyl aziridines having both α- and β-protons decomposed when treated with LDA in either tetrahydrofuran or hexamethylphosphoramide. However, when α-protons were not present, allylic amine was formed, presumably via β-elimination.
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