Reactions of 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine with linear and cyclic 1,3-diketones |
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Authors: | Liane M. Grieco Gary A. Halliday Christopher P. Junk Steven R. Lustig William J. Marshall Viacheslav A. Petrov |
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Affiliation: | aDuPont Central Research and Development,1 Experimental Station, PO Box 80500, Wilmington, DE 19880-0500, United States;bDuPont Corporate Center for Analytical Sciences, Experimental Station, PO Box 80500, Wilmington, DE 19880-0500, United States |
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Abstract: | Ketones are known to be unreactive toward α-fluoroamines such as Ishikawa's Reagent or 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine (TFEDMA). On the other hand, 1,3-diketones were found to undergo fluorination with TFEDMA. In the case of linear 1,3-diketones, the proposed mechanism involves the formation of β-fluoro-α,β-unsaturated ketones followed by the addition of HF to selectively give the product β,β-difluoroketone. Interestingly, when the 1,3-diketone is cyclic (i.e. 1,3-cyclohexadione) the outcome of the reaction is different and results in the formation of a product with a 2,2-difluoroacetyl group on the 2-carbon. |
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Keywords: | 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine TFEDMA Fluorination 1,3-Diketone 1,3-Cyclohexanedione β,β-Difluoroketone β-Fluoro-α,β-unsaturated ketones Ishikawa's Reagent |
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