Related Experiment Video
Updated: Dec 11, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of azetidines by aza Paternò-Büchi reactions
Alistair D Richardson1, Marc R Becker1, Corinna S Schindler1
1Willard Henry Dow Laboratory , Department of Chemistry , University of Michigan , Ann Arbor , MI 48109 , USA .
Abstract:
The [2 + 2] photocycloaddition reaction between an imine and an alkene component, the aza Paternò-Büchi reaction, is one of the most efficient ways to synthesize functionalized azetidines. However, the application of the aza Paternò-Büchi reaction has been met with limited success due to the inherent challenges associated with this approach. This review covers the current scope and limitations of reported examples of aza Paternò-Büchi reactions in organic synthesis. An outlook is provided, which highlights recent improvements and the discovery of new reaction protocols that have overcome some long-standing challenges within this field of research.
More Related Videos
Related Concept Videos
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...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

