Reactions of perfluorome thacrylic acid derivatives with hydroxy and mercapto compounds

Autor: Utebaev, U., Rokhlin, E. M., Lur'e, É. P.
Zdroj: Russian Chemical Bulletin; January 1976, Vol. 25 Issue: 1 p129-134, 6p
Abstrakt: 1.Perfluoromethacrylic acid derivatives (methyl ester and dimethylamide) easily add carboxylic acids at the C=C bond to give comparatively stablea-hydro-ß-acyloxypentafluoroisobutyric acid derivatives. These adducts when heated are cleaved to the corresponding acyl fluoride anda-hydro-a-fluorocarbonyltrifluoropropionic acid derivative.2.Hydrogen chloride adds to the perfluoromethacrylic acid dimethylamide to give thea-hydro-ß-chloropentafluoroisobutyric acid derivative. The perfluoromethacrylic acid ester reacts in a similar manner only in the presence of a base.3.The perfluoromethacrylic acid dimethylamide when reacted with phenol, thiophenol, and benzyl mercaptan gives the substitution products of the vinyl fluorine atom (mixture of cis and trans isomers), while with pentafluorophenol it gives a mixture of substitution and addition products.4.The reaction rate of the perfluoromethacrylic acid dimethylamide with nucleophiles decreases in the order: RCOOH > AlkOH > C6H5SH > C6F5OH > C6H5CH2SH > C6H5OH » (CF3)2CHOH.
Databáze: Supplemental Index
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