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Updated: Aug 1, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
New Insight into the Reactivity of S,S-Bis-ylide
Ugo Authesserre1, V S V S N Swamy1, Nathalie Saffon-Merceron2
1Université de Toulouse, UPS, and CNRS, LHFA UMR 5069, 118 Route de Narbonne, 31062 Toulouse, France.
Abstract:
The present work focuses on the reactivity of S,S-bis-ylide 2, which presents a strong nucleophilic character, as evidenced by reactions with methyl iodide and CO2, affording C-methylated salts 3 and betaine 4, respectively. The derivatization of betaine 4 affords the corresponding ester derivative 6, which is fully characterized by using NMR spectroscopy and X-ray diffraction analysis. Furthermore, an original reaction with phosphenium ions leads to the formation of a transient push-pull phosphino(sulfonio)carbene 8, which rearranges to give stabilized sulfonium ylide derivative 7.
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