New Insight into the Reactivity of S,S-Bis-ylide

Ugo Authesserre (1) , V S V S N Swamy (1) , Nathalie Saffon-Merceron , Antoine Baceiredo (1) , Tsuyoshi Kato (1) , Eddy Maerten (1)

1 LHFA - Laboratoire Hétérochimie Fondamentale et Appliquée

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.

Keywords: bis-ylides ylide carbone phosphenium carbene; bis-ylides; ylide; carbone; phosphenium; carbene

Domains: Chemical Sciences

Ugo Authesserre, V S V S N Swamy, Nathalie Saffon-Merceron, Antoine Baceiredo, Tsuyoshi Kato, et al.. New Insight into the Reactivity of S,S-Bis-ylide. Molecules, 2023, 28 (8), pp.3295. ⟨10.3390/molecules28083295⟩. ⟨hal-04067288⟩