Liqiang Wu, Yongxue Wang, Fu‐Lin Yan
May 20, 2010
Citations
0
Influential Citations
10
Citations
Journal
Bulletin of The Korean Chemical Society
Abstract
have also been applied to the conversion of oxiranes into thiiranes. Nevertheless, most of these methods suffer one or more of the following draw-backs: unsatisfactory yield, long reaction time, critical product isolation procedures, the use of expensive and detrimental metal precursors, harsh reaction conditions, and no agreement with the green chemistry protocols, which limit their use.Etidronic acid (Figure 1) is a phosphonic acid with mild aci-dity, is non-volatile and non-corrosive, and is soluble in common organic solvents. It is a white crystalline solid with outstanding physical and chemical properties and is a commercially avail-able cheap chemical. Its applications as a reaction catalyst in organic syntheses have not yet been fully explored. In this paper,we report a simple and efficient synthesis of thiiranes in THFusing etidronic acid as a catalyst (Scheme 1).Initially, we carried out the reaction of styrene oxide with ammonium thiocyanate in THF in the presence of different amounts of etidronic acid at reflux temperature. It was found that the best result was obtained with 10 mol % of etidronic acid.It is worthy to note that in the absence of etidronic acid, the reaction did not yield any product at reflux temperature even after a long reaction time. To select the best solvent for the reaction, the synthesis of thiirane