Synlett

Synthesis of lithium 1-alkynesulfenates by the mild oxidation of thiolates with a pinacolone-derived N-sulfonyloxaziridine

…, C Boudou, C Caupene, MT Averbuch-Pouchot…

Index: Sandrinelli, Franck; Boudou, Cedric; Caupene, Caroline; Averbuch-Pouchot, Marie-Therese; Perrio, Stephane; Metzner, Patrick Synlett, 2006 , # 19 p. 3289 - 3293

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Citation Number: 4

Abstract

Abstract Lithium 1-alkynethiolates, generated by a base-induced ring cleavage of 4- substituted 1, 2, 3-thiadiazoles, were efficiently converted into the corresponding sulfenate salts by mild oxidation using an N-sulfonyloxaziridine derived from pinacolone. In situ S- alkylation with alkyl halides led to α, β-acetylenic sulfoxides.