121671-61-2Relevant academic research and scientific papers
METHODE GENERALE D'ACCES AUX TRIFLUOROMETHYLCETONES. 1ere PARTIE: ALKYLATION DIRECTE DU TRIFLUOROACETYLACETATE D'ETHYLE
Aubert, Corinne,Begue, Jean-Pierre,Charpentier-Morize, Micheline,Nee, Gerard,Langlois, Bernard
, p. 361 - 376 (1989)
Alkylation of Ethyl 4,4,4 trifluoroacetylacetate (ETFAA) 1 by alkyl halides presented some typical features.The reaction was very slow and led preferentially to O-alkylated products.However, with activated halides and under some peculiar conditions, it was possible to obtain selectively C-alkylated products 3 and 4 in good yields.
Alkylation of Ethyl 4,4,4-Trifluoroacetoacetate. First Example of a Reversible O-Alkylation Process leading to C-Alkylation
Begue, Jean-Pierre,Charpentier-Morize, Micheline,Nee, Gerard
, p. 83 - 84 (2007/10/02)
In aprotic polar solvents the ratio of O vs.C alkylation products of ethyl 4,4,4-trifluoroacetoacetate (ETFAA) can be dependent on reaction time; in hexamethylphosphoric triamide (HMPA) or acetone, the SN2 cleavage of enol ethers of ETFAA with sodium iodide was observed with concomitant formation of the sodium enolate and the corresponding iodides, and in the case of an activated iodide the mono- and di-alkylation products resulted quantitavely.
