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

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• 作者：Cé ; dric Boudou ; Matthieu Bergè ; s ; Charlè ; ne Sagnes ; Jana Sopkov&aacute ; -de Oliveira Santos ; Sté ; phane Perrio ; Patrick Metzner
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：July 6, 2007
• 年：2007
• 卷：72
• 期：14
• 页码：5403 - 5406
• 全文大小：83K
• 年卷期：v.72,no.14(July 6, 2007)
• ISSN：1520-6904

文摘

Aliphatic thiolates were efficiently converted into the corresponding sulfenates by smooth oxidation with trans-(±)-2-tert-butyl-3-phenyloxaziridine at room temperature (fiveexamples). Subsequent electrophilic quench with benzylbromide led to sulfoxides (S-alkylation) in good to moderateyields. Application of the protocol to an aromatic substratewas also successful. This work represents the first valuableexample of the use of this poorly active oxidizing agent insynthetic organic chemistry without the need for activatingconditions.