Reactions of 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine with linear and cyclic 1,3-diketones
2011; Elsevier BV; Volume: 132; Issue: 12 Linguagem: Inglês
10.1016/j.jfluchem.2011.06.011
ISSN1873-3328
AutoresLiane M. Grieco, Gary A. Halliday, Christopher P. Junk, Steven R. Lustig, William Marshall, Viacheslav A. Petrov,
Tópico(s)Synthesis and Reactions of Organic Compounds
ResumoKetones 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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