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Synthèse de monoalcools et de monoacides chlorofluorés par télomérisation avec des telogènes chlorofluorés

1981; Wiley; Volume: 182; Issue: 11 Linguagem: Inglês

10.1002/macp.1981.021821101

0025-116X

Bernard Boutevin, Jean‐Pierre Hugon, Y. Piétrasanta,

Inorganic Fluorides and Related Compounds

Abstract Telomerizations of chlorofluorinated telogens CF 3 CCl 3 and \documentclass{article}\pagestyle{empty}\begin{document}$${\rm Cl\rlap{--} (CFCl \hbox{---} CF}_{\rm 2} {\rm \rlap{--} )}_{\rm n} {\rm CCl}_{\rm 3}$$\end{document} (1 ≤ n ≤ 4) with acrylic, allylic, and vinylic monomers were studied. With allyl alcohol and 2‐hydroxyethyl acrylate the corresponding fluorinated adducts 1 and 2 were obtained directly. Vinyl and allyl acetates led to the adducts 4a , b and 5a , b , respectively, which could be transformed into the corresponding acetals and alcohols. Telomerizations of methyl acrylate and methacrylate led to the fluorinated adducts 12a and b in the presence of copper chloride as catalyst or also with iron trichloride in the case of methyl methacrylate. By intramolecular elimination the methacrylate adducts were transformed into the lactons 13 and 14 and the acrylate adducts by reduction into the alcohols 1 and 2 . The same reduction of the methacrylate adduct led to the 2,4,4‐trichloro‐5,5,5‐trifluoro‐2‐methyl‐1‐pentanol ( 15 ). Independent on the applied catalyst the telomerization of vinylacetic acid led to the monoaddition product, whereas in the case of methacrylic or acrylic acid the formation of monoadducts or higher addition products was found to depend on the catalyst.