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Cis-trans isomerization of an α,α-difluoroolefin catalyzed by bromine

✍ Scribed by Marek Masnyk; Josef Fried

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
211 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The cis-trans isomerization of 1 by Br2 in CC14 is described. A bridged bromonium cation a to CF, is destabilized resulting-in a carbocation bromide ion pair at the B-carbon capable of freg rotation and loss of bromine to form 2. A CF2 group appears to be more effective in promoting isomerization than aryl in the case of stilbenes.

We recently described a synthesis of (Z)-7,7-difluoro-8-dodecenyl acetate (I), a fluoro derivative of the sex pheromone of the oriental fruit moth and its photo isomerization to the E-isomer 2.

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