911308-63-9Relevant academic research and scientific papers
Novel synthesis, reactivity, and stereochemistry of substituted 3-trifluoromethyl- and 3-perfluoroalkyl-3-phenoxyprop-2-enal
El Kharrat, Salem,Laurent, Philippe,Blancou, Hubert
, p. 6742 - 6752 (2006)
Substituted 3-phenoxy-3-perfluoroalkylprop-2-enals 3a-s are synthesized in high yields starting from a gem-iodoacetoxy derivative 1 and phenoxides 2. Then efficient syntheses of push-pull derivatives 4, 5, 8a,b, and nonconjugated analogues 6 and 7 illustrate the synthetic potentialities of 3. Stereochemical studies of these perfluoroalkyl-containing trisubstituted olefinic derivatives 3-8b revealed that the 4JCF coupling constant observed in the 13C NMR spectra was crucial in the determination of their configurations and conformations in solution. The solvent polarity effect on the stereochemistry of push-pull compounds 3-5 and 8a,b was studied. Unusual significant medium polarity effect on the stereochemistry of imino enol ether derivative 4 was observed.
