α-Trifluoroacetyl-δ-valerolactone: synthesis, acyl-lactone rearrangement and unexpected easy decarboxylation of the rearranged product |
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Authors: | Dmitri V Sevenard Enno Lork |
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Affiliation: | Institute of Inorganic & Physical Chemistry, University of Bremen, Leobener Strasse, 28334 Bremen, Germany |
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Abstract: | Claisen condensation of δ-valerolactone and ethyl trifluoroacetate leads to α-trifluoroacetyl-δ-valerolactone, existing completely in CDCl3 solution as an enol. Upon treatment of this cyclic 1,3-ketoester with aqueous HCl, an acyl-lactone rearrangement takes place. The structure of the resulting pyran was confirmed by an X-ray analysis. The ability of the rearrangement product to lose its carboxylic group under unexpected mild conditions was used for the synthesis of the corresponding 3-unsubstituted cyclic hemi-ketal. |
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Keywords: | Fluorinated 1,3-ketoesters Lactones Enol Acyl-lactone rearrangement Pyrans X-ray analysis |
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