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Updated: May 29, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Claisen rearrangements of equilibrating allylic azides
Donald Craig1, John W Harvey, Alexander G O'Brien
1Department of Chemistry, Imperial College London, South Kensington Campus, London, UK SW7 2AZ. d.craig@imperial.ac.uk
Abstract:
Equilibrating mixtures of allylic azide-containing allylic alcohols or allylic 2-tolylsulfonylacetic esters undergo Johnson-Claisen or Ireland-Claisen rearrangement reactions to give unsaturated γ-azidoesters and -acids, respectively. Decarboxylation of the acids under basic conditions gives azidosulfones, with moderate to high diastereoselectivity.
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