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Nouveaux accès aux ions sulfinates et sulfénates

Abstract : Sulfenate (RSO–) and sulfinate salts (RSO2–) are very useful sulfur nucleophiles, as precursors of sulfoxides and sulfones respectively (S-alkylation). My PhD work allowed the development of a straightforward access to alkanesulfinate anions by oxidation of the corresponding thiolates. An N-sulfonyloxaziridine derived from pinacolone was identified as the ideal reagent. The alkylation of the sulfinates salts by treatment with alkyl halides was investigated. A general method for the generation of sulfenate salts has been developed starting with sulfoxides possessing an activating fonction in b-position. The methodology is based on an elimination reaction initiated by a base at low temperature. According to the simplicity of the protocol, a large range of sulfenate salts has been prepared. Finally, preliminary results of sulfenate formation starting with b-silylated sulfoxides were very promising in the aromatic series.
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Contributor : Caroline Caupène <>
Submitted on : Monday, December 10, 2007 - 10:53:27 AM
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  • HAL Id : tel-00195177, version 1


Caroline Caupène. Nouveaux accès aux ions sulfinates et sulfénates. Autre. Université de Caen, 2005. Français. ⟨tel-00195177⟩



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