Molecules (Apr 2023)
New Insight into the Reactivity of S,S-Bis-ylide
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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