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Regioselective and stereospecific opening of an oxirane system mediated by trifluoroacetic acid and halide anions. A new direct approach to C3-vicinal halohydrins |
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| Authors: | Stephan D. Stamatov Jacek Stawinski |
| Affiliation: | 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: | Glycidol derivatives bearing ester, ether or silyl functionality upon treatment with trifluoroacetic acid (TFA) in the presence of a halide anion (e.g., Bu4NX; X = Cl, Br or I) at room temperature undergo regioselective and stereospecific opening of the oxirane ring to produce the corresponding C3-vicinal haloalkanols in practically quantitative yields. |
| Keywords: | Glycidol derivatives Trifluoroacetic acid Tetra-n-butylammonium halides C3-Vicinal halohydrins |
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