Applications of cyclic sulfates of vic-diols: synthesis of episulfides, olefins, and thio sugars

…, P García-Mendoza, F Hernández-Mateo…

Index: Calvo-Flores, Francisco G.; Garcia-Mendoza, Pilar; Hernandez-Mateo, Fernando; Isac-Garcia, Joaquin; Santoyo-Gonzalez, Francisco Journal of Organic Chemistry, 1997 , vol. 62, # 12 p. 3944 - 3961

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Citation Number: 61

Abstract

A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic ...

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