Preparation of 3-substituted and 2,3-disubstituted-4,4,4-trifluoro-2-butenoic acids—Perkin condensation of activated aromatic ketones

Cserényi, Szabolcs and Felföldi, Károly and Forgó, Péter and Pálinkó, István (2006) Preparation of 3-substituted and 2,3-disubstituted-4,4,4-trifluoro-2-butenoic acids—Perkin condensation of activated aromatic ketones. JOURNAL OF FLUORINE CHEMISTRY, 127 (7). pp. 850-853. ISSN 0022-1139

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Abstract

The Perkin reaction of the activated aromatic ketones (2,2,2-trifluoroacetophenone and its 4'-phenyl-derivative) with various condensing agents (acetic anhydride, propionic anhydride, phenylacetic acid/acetic anhydride) gives the title compounds in good or moderate yields, and high E-stereoselectivity. For some derivatives an appreciable amount of the Z isomer was also formed. Several of the resulting butenoic acids and their methyl esters are synthesised and characterised for the first time.

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