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Mechanistic investigation of the NH-sulfoximination of sulfide. Evidence for λ6-sulfanenitrile intermediates

Abstract : We report a new procedure for the preparation of NH-sulfoximines from sulfides using PIDA as an oxidant and ammonium carbamate as the ammonia source. Excellent yields were obtained with a wide range of sulfides. The formation of acetoxy- and methoxy-λ6-sulfanenitrile as intermediates was proposed, both of which were converted to the NH-sulfoximine by the action of the solvent. The structure of these intermediates was confirmed by 1H, 13C and 15N NMR and HRMS analysis.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02376142
Contributor : Vincent Reboul <>
Submitted on : Friday, November 22, 2019 - 1:32:11 PM
Last modification on : Thursday, July 2, 2020 - 3:21:26 AM

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Jean-François Lohier, Thomas Glachet, Hamid Marzag, Annie-Claude Gaumont, Vincent Reboul. Mechanistic investigation of the NH-sulfoximination of sulfide. Evidence for λ6-sulfanenitrile intermediates. Chemical Communications, Royal Society of Chemistry, 2017, 53 (12), pp.2064-2067. ⟨10.1039/c6cc09940h⟩. ⟨hal-02376142⟩

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