Isomerisation reaction of a gem-bis-trifluoromethyl olefin in a basic medium: a kinetic study

M Tordeux, L Marival-Hodebar, MJ Pouet…

Index: Tordeux, Marc; Marival-Hodebar, Laurence; Pouet, Marie-Josee; Halle, Jean-Claude; Wakselman, Claude Journal of Fluorine Chemistry, 2001 , vol. 111, # 2 p. 147 - 152

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Abstract

The rearrangement of 5-phenyl-1, 1, 1-trifluoro-2-(trifluoromethyl) pent-2-ene to 5-phenyl-1, 1, 1-trifluoro-2-(trifluoromethyl) pent-3-ene has been studied by 19 F NMR in dimethylsulphoxide (DMSO). This isomerisation is catalysed by a base such as triethylamine. It is apparent that the olefin is more stable when the two trifluoromethyl groups are placed on a saturated carbon rather than on a vinylic carbon. In the isomerisation ...

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