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Updated: Sep 30, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Relative stabilities of some synthetically useful 2,3-cis-disubstituted aziridines and their 2,3-trans isomers
Norio Mimura1, Yoshihisa Miwa, Toshiro Ibuka
1Faculty of Pharmaceutical Sciences, Kyoto University, Japan. Norio.Mimura@pharma.novartis.com
Abstract:
The relative stabilities of synthetically useful 2,3-cis/trans pairs of 2,3-disubstituted aziridines were investigated theoretically by performing molecular orbital calculations at the MP2/6-31G**/RHF/6-31G** level of theory. The results showed clearly that a functional group on the nitrogen atom of the aziridine ring plays a very important role in conjunction with the relative stabilities of these pairs of isomers. There is a tendency that the 2,3-cis isomer bearing tetrahedral structure on the aziridine nitrogen is preferable. Bulky substituents such as a phenyl group on aziridine atoms can also affect the relative stability sterically.
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