Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 8, Pages 4171-4176Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400280p
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Funding
- Fundamental Research Funds for the Central Universities [DUT13LAB03]
- SRF for ROCS, SEM
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A highly efficient, operationally simple approach to trifluoromethyl ketones has been developed that builds on the use of a tandem process involving Claisen condensation and retro-Claisen C-C bond cleavage reaction. Enolizable alkyl phenyl ketones were found to react readily with ethyl trifuoroacetate under the promotion of NaH to afford trifluoroacetic ester/ketone exchange products, trifluoromethyl ketones, which were quite different from the general Claisen condensation products, beta-diketones. This procedure uses readily available starting materials and can be extended to the preparation of perfluoroalkyl ketones in excellent yield.
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