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Updated: Sep 29, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Isomerization of Aziridines to Allyl Amines via Titanium and Chromium Cooperative Catalysis
Chengbo Yao1, Alana D N Williams1, Yiting Gu1
1Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027, United States.
Abstract:
A Ti/Cr cooperative catalyst isomerizes aziridines to allyl amines under mild conditions. The reaction tolerates a broad range of aziridines with various nitrogen substituents. The titanium catalyst is most successful in opening 1,2-disubstituted aziridines, forming radical intermediates in a highly regioselective manner. The chromium catalyst appears to abstract an H• from these radical intermediates and then return the H• to the titanium system in the form of an H+ and an electron. The reaction is complementary to previous reports on the isomerization of aziridines to allyl amines.
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