trans-(±)-2-tert-Butyl-3-phenyloxaziridine: A Unique Reagent for the Oxidation of Thiolates into Sulfenates

…, C Sagnes, J Sopková-de Oliveira Santos…

Index: Boudou, Cedric; Berges, Matthieu; Sagnes, Charlene; Sopkova-De Oliveira Santos, Jana; Perrio, Stephane; Metzner, Patrick Journal of Organic Chemistry, 2007 , vol. 72, # 14 p. 5403 - 5406

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Citation Number: 17

Abstract

Aliphatic thiolates were efficiently converted into the corresponding sulfenates by smooth oxidation with trans-(±)-2-tert-butyl-3-phenyloxaziridine at room temperature (five examples). Subsequent electrophilic quench with benzyl bromide led to sulfoxides (S-alkylation) in good to moderate yields. Application of the protocol to an aromatic substrate was also successful. This work represents the first valuable example of the use of this poorly active ...