Related Experiment Video
Updated: Aug 19, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Stereocontrolled synthesis of angularly substituted 1-azabicyclic rings by cationic 2-aza-cope rearrangements
Zachary D Aron1, Larry E Overman
1Department of Chemistry, University of California-Irvine, 516 Rowland Hall, Irvine, CA 92697-2025, USA.
Abstract:
A new synthesis of 1-azabicyclic molecules having angular substitution is reported. This method can be employed to prepare a range of 1-azabicylic rings, including ones containing vicinal quaternary carbon centers and three contiguous stereocenters. [structure: see text]
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
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...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

