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Updated: Aug 21, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of carboalkoxychloro- and bromodiazirines
Tomas Martinu1, William P Dailey
1Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. dailey@sas.upenn.edu
Abstract:
The first known 3H-diazirines bearing a carbonyl group and a halogen atom on C-3 have been prepared by a novel synthetic method. Carboalkoxychloro- and bromodiazirines 1a-d are formed in up to 45% yields by reductive dechlorination of carboalkoxy-N,N,N'-trichloroformamidines 9a,b using chloride or bromide ion. This method constitutes the first example of the use of N,N,N'-trichloroamidines as starting materials in organic synthesis.
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