Journal of organometallic chemistry

2-Diethoxyphosphoryl alcanoic acid dianions (lithium α-lithiocarboxylates): IV. A direct route to 2-fluoro-2-alkenoic acids by the Horner synthesis. Application in the …

P Coutrot, C Grison, R Sauvêtre

Index: Coutrot, Ph.; Grison, C.; Sauvetre, R. Journal of Organometallic Chemistry, 1987 , vol. 332, p. 1 - 8

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Abstract

Abstract 2-Diethoxyphosphoryl-2-fluoroacetic acid was converted into the lithium α lithiocarboxylate dianion by treatment with n-butyllithium in hexane/tetrahydrofuran at− 70 C. The Horner reaction between this new dianion and carbonyl compounds gave various 2- fluoro-2-alkenoic acids. Application of the method to the cis, trans caronaldehyde ethyl esters led to the 2-fluoroethenyl pyrethroid derivatives (Z, cis, E-cis, Z-trans, E-trans).

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