Synthesis and Applications of Perfluoro-oxa-alkylated Compounds.
Open Access
- 1 January 1992
- journal article
- Published by The Society of Synthetic Organic Chemistry, Japan in Journal of Synthetic Organic Chemistry, Japan
- Vol. 50 (7) , 592-603
- https://doi.org/10.5059/yukigoseikyokaishi.50.592
Abstract
Perfluoro-oxa-alkanoyl peroxides were prepared from the corresponding acyl fluorides and hydrogen peroxide under alkaline condition. The decomposition of these peroxides was found to occur more easily in comparison with those of perfluoroalkanoyl peroxides such as perfluorooctanoyl peroxide. Perfluoro-oxa-alkanoyl peroxides could be used as a reagent for perfluoro-oxa-alkylation of aromatic compound such as benzene, thiophene, furan, or pyrrole, and were found to be applied to direct aromatic perfluoro-oxa-alkylation of polystyrene in the same manner as with perfluoroalkanoyl peroxides. Furthermore, both perfluoro-oxa-alkanoyl peroxides and perfluoroalkanoyl peroxides were shown to be a usuful reagent for the generation of perfluoro-oxa-alkyl and perfluoroalkyl radicals, and to be used for the introduction of perfluoro-oxa-alkyl and perfluoroalkyl groups into monomers possessing lower HOMO energy levels than that of styrene such as vinylsilanes, 3-methacryloxypropylsilane, 3-acryloxypropylsilane, and acrylic acid Especially, perfluoro-ox-a-alkylated aromatic and silicon compounds exhibited excellent surface activity not shown by the perfluoroalkylated ones.Keywords
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