Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions
Related Experiment Video
Updated: Mar 13, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Otome E Okoromoba1, Zhou Li1, Nicole Robertson1
1Department of Chemistry, University of Louisville, Louisville, KY 40292, USA. gb.hammond@louisville.edu.
Abstract:
We developed an efficient fluorination protocol that converts easily accessible aziridines into β-fluoroamines, which are important motifs in biologically active molecules. In contrast with traditional fluorination approaches, DMPU-HF has shown both higher reactivity and regioselectivity and good functional group tolerance; thus, a wide scope of β-fluoroamines can now be accessed conveniently. The stereochemical behavior of the ring opening depends on the substitution pattern of the aziridine substrate.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

