Synthesis and Comparison of the Reactivity of Allyl Fluorides and ...

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Chapter Two
after purification via column chromatography [hexane: diethyl ether (85:15)]. All three
products exhibited a characteristic signal at ca. – 185 ppm in their 19 F{ 1 H} NMR spectra
(Table 2.9).
Starting
Substrate
(69)
(68)
(70)
(71)
Product Yield (%)
(72)
(73)
(74)
(75)
Table 2.9 Yields obtained of fluorinated products (72)-(75)
2.2.1.2 Synthesis of Derivatised Allyl Benzoates
After synthesising several allylic fluorides as conducted by Gouverneur, it was found that
there was the possibility of creating a new library of allylic fluoride compounds which were
derivatised on the benzoate ring. It could then be observed whether functionalisation of the
ring had an effect on the allylic portion of the substrate in reactions with palladium in
0
33
77
55