Ring opening of epoxides with NaHSO4: isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols

• DOI: 10.1016/j.tet.2008.11.092
• Publication Date: 2008-12-05T06:58:29Z
• Authors: Huseyin Cavdar; Nurullah Saracoglu
• Keywords: Hydrogen Sulfate; Vicinal

Abstract Sodium hydrogen sulfate (NaHSO 4 ) was observed to be highly effective as a reagent or catalyst in the ring-opening reactions of epoxides under mild conditions. Reaction of epoxides with NaHSO 4 gave isolable β-hydroxy sulfate esters and vicinal diols. Experimenting with different epoxides, the study investigated the scope of the ring-opening reaction.