Synthesis of 1,1,1-trichloro[fluoro]-3-alken-2-ones using ionic liquids

i: Pyridine (1 equiv.), [BMIM]·BF 4 or [BMIM]·PF 6 (0.1 equiv.), 0° to r.t., 1.5 h. ▪ The synthesis of a series of ten 1,1,1-trichloro[fluoro]-3-alken-2-ones [CX 3C(O)C(R 2) C(R 1)OR, where X = Cl and F; R 1/R 2/R = H/H/Et, Me/H/Me, H/Me/Et, H/ (CH 2) 2 and H/ (CH 2) 3 ] from the acylation reactions...

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Bibliographic Details
Published in:Journal of molecular catalysis. A, Chemical Chemical, 2007-04, Vol.266 (1), p.100-103
Main Authors: Martins, Marcos A.P., Guarda, Emerson A., Frizzo, Clarissa P., Scapin, Elisandra, Beck, Paulo, da Costa, Alexandre C., Zanatta, Nilo, Bonacorso, Helio G.
Format: Article
Language:English
Subjects:
Acylation
Catalysis
Chemistry
Exact sciences and technology
General and physical chemistry
Ionic liquid
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Trihalomethyl compounds
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Summary:i: Pyridine (1 equiv.), [BMIM]·BF 4 or [BMIM]·PF 6 (0.1 equiv.), 0° to r.t., 1.5 h. ▪ The synthesis of a series of ten 1,1,1-trichloro[fluoro]-3-alken-2-ones [CX 3C(O)C(R 2) C(R 1)OR, where X = Cl and F; R 1/R 2/R = H/H/Et, Me/H/Me, H/Me/Et, H/ (CH 2) 2 and H/ (CH 2) 3 ] from the acylation reactions of enol ethers with trichloroacetyl chloride or trifluoroacetic anhydride in the presence of equimolar amounts of pyridine and 10% mol-equiv. of imidazolium based ionic liquid [BMIM]·BF 4 or [BMIM]·PF 6 is reported. The reaction time, the ionic liquid recyclation and yields were investigated and this method showed advantages over the methods described in the literature.
ISSN:1381-1169
1873-314X
DOI:10.1016/j.molcata.2006.10.053