Further studies on the synthesis of α-fluoro carbonyl compounds [1] |
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Authors: | Gary L. Cantrell Robert Filler |
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Affiliation: | Department of Chemistry, Illinois Institute of Technology, Chicago, Illinois 60616 U.S.A. |
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Abstract: | The trimethylsilyl enol ethers of cycloalkanones and acid esters are converted in high yields (70–90%) to the corresponding α-fluoro carbonyl derivative using XeF2 in CH2Cl2. Non-cyclic α-hydroxy ketones such as ethyl mandelate are efficiently transformed to the α-fluoro product by DAST and by Ishikawa's reagent. Nucleophilic displacement of halogen by fluoride failed in cyclic systems, giving instead, α,β-unsaturated ketones in DMF or CH3CN (18-crown-6) and 1,2-diones in DMSO, with KF acting as a base. Attempts at DMSO oxidation of I(Br)F adducts failed to give the α-fluoro ketones, but resulted in dehydrohalogenation to the -vinyl fluorides. |
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