Regioselective alkylation of the trifluoromethyl analog of Hagemann’s ester

The reactivity of the enolate of the 4-carbethoxy-3-trifluoromethyl-cyclohex-2-enone ( 1) toward electrophiles has been studied and compared with that of the parent Hagemann’s ester. Presence of the CF 3 group could allow the selective introduction of substituents at three different sites. With alky...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2001-03, Vol.108 (1), p.91-94
Main Authors: Legros, Julien, Barhoumi-Slimi, Thouraya, Crousse, Benoı̂t, Bonnet-Delpon, Danièle, El Gaied, Moncef, Bégué, Jean-Pierre
Format: Article
Language:English
Subjects:
Cyclohexenone
Enolate alkylation
Fluorinated phenol
Hagemann’s ester
Trifluoromethyl
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Summary:The reactivity of the enolate of the 4-carbethoxy-3-trifluoromethyl-cyclohex-2-enone ( 1) toward electrophiles has been studied and compared with that of the parent Hagemann’s ester. Presence of the CF 3 group could allow the selective introduction of substituents at three different sites. With alkyl halides the C-2 alkylation is completely favored. High selectivity is directed to the C-4 site with ethyl chloroformate, and only O-silylation occurred with a silylated chloride.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(01)00344-X