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Efficient, highly regioselective, and stereospecific conversion of glycidol systems into C2-O-acylated vicinal halohydrins |
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| Authors: | Stephan D Stamatov |
| Institution: | a Department of Chemical Technology, University of Plovdiv, 24 Tsar Assen St., Plovdiv 4000, Bulgaria b Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden c Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznan, Poland |
| Abstract: | Glycidyl esters and ethers undergo a regioselective and stereospecific opening of the oxirane ring upon treatment in chloroform in the presence of pyridine with trimethylsilyl halide (TMSX, X = Cl, Br, or I) and a mixture of carboxylic acid (CA)-trifluoroacetic anhydride (TFAA), to produce the corresponding C2-O-acylated vicinal halohydrins in high yields. |
| Keywords: | Glycidol Trimethylsilyl halides Trifluoroacetic anhydride Carboxylic acids Vicinal haloesters |
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