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Updated: Aug 14, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
1,2-Diamination of Alkenes via 1,3-Dipolar Cycloaddition with Azidium Ions or Azides
Setareh Saryazdi1, Sean Parkin1, Robert B Grossman1
1Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506-0055, United States.
Abstract:
We describe two new methods for the 1,2-diamination of alkenes. First, either an azidium ion (ArN═N+═NAr) undergoes 1,3-dipolar cycloaddition with an alkene to give a 1,2,3-triazolinium ion directly, or an intramolecular azide-alkene cycloaddition followed by N-benzylation provides the same. Second, hydrogenation of the 1,2,3-triazolinium ion over Raney Ni excises the central N atom and gives the 1,2-diamine. The stereochemistry of the alkene is usually, but not always, preserved in the 1,2-diamine.
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