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- Novel synthesis, reactivity, and stereochemistry of substituted 3-trifluoromethyl- and 3-perfluoroalkyl-3-phenoxyprop-2-enal

Auteur(s): El Kharrat S., Laurent P., Blancou H.

(Article) Publié: European Journal Of Organic Chemistry, vol. 71 p.6742-6752 (2006)


Résumé:

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 (4)J(CF) coupling constant observed in the C-13 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.



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