Influence of Homoallylic Fluorine Atoms on the Regioselectivity of the Wacker Reaction

J.      Guidotti; M.      Tordeux; J.-   C.   Blazejewski; C.      Wakselman

doi:10.2174/1570178053203008

Abstract

Wacker oxidation reaction of terminal olefins bearing one or two fluorine atoms at a homoallylic position led to a ratio aldehyde/methyl ketone much higher than that observed with their non-fluorinated analogues. This regioselectivity can be ascribed to a specific interaction between fluorine atoms and palladium, or to a peculiar influence of the halogens on the double bond.

Keywords: wacker reaction, palladium, fluorine, regioselectivity

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Letters in Organic Chemistry

Title: Influence of Homoallylic Fluorine Atoms on the Regioselectivity of the Wacker Reaction

Volume: 2 Issue: 2

Author(s): J. Guidotti, M. Tordeux, J.- C. Blazejewski and C. Wakselman

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Keywords: wacker reaction, palladium, fluorine, regioselectivity

Abstract: Wacker oxidation reaction of terminal olefins bearing one or two fluorine atoms at a homoallylic position led to a ratio aldehyde/methyl ketone much higher than that observed with their non-fluorinated analogues. This regioselectivity can be ascribed to a specific interaction between fluorine atoms and palladium, or to a peculiar influence of the halogens on the double bond.

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Guidotti J., Tordeux M., Blazejewski C. J.- and Wakselman C., Influence of Homoallylic Fluorine Atoms on the Regioselectivity of the Wacker Reaction, Letters in Organic Chemistry 2005; 2 (2) . https://dx.doi.org/10.2174/1570178053203008