Reactions of perfluorome thacrylic acid derivatives with hydroxy and mercapto compounds

Autor: E. P. Lur'e, U. Utebaev, E. M. Rokhlin
Rok vydání: 1976
Předmět:
Zdroj: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science. 25:129-134
ISSN: 1573-9171
0568-5230
DOI: 10.1007/bf00925634
Popis: 1. Perfluoromethacrylic acid derivatives (methyl ester and dimethylamide) easily add carboxylic acids at the C=C bond to give comparatively stableα-hydro-β-acyloxypentafluoroisobutyric acid derivatives. These adducts when heated are cleaved to the corresponding acyl fluoride andα-hydro-α-fluorocarbonyltrifluoropropionic acid derivative. 2. Hydrogen chloride adds to the perfluoromethacrylic acid dimethylamide to give theα-hydro-β-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: OpenAIRE
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