1985 Volume 1985 Issue 10 Pages 1958-1962
Bis(heptafluorobutyryl) peroxide [1] has been widely used as an initiator of radical polymerization of vinyl chloride or fluorine-substituted olefins. However, the study on the decomposition of [1] itself is few. Mechanism of the decomposition of [1] was investigated by reaction rate study. The homolytic decomposition of [1] easily occurred in comparison with that of the corresponding nonfluorinated diacyl peroxide. The peroxide [1] underwent readily decomposition induced by nucleophilic reagents such as benzenes with electron-donating substituents or water (Fig.1 and Table 1). This property may be attributed to that the high electronegativity of perfluoroalkyl group lowers the energy level of antibonding O-O orbital and increases the positive charge on carbonyl carbon atom. The reaction of [1] with benzenes gave perfluoropropylbenzenes in good yields, so the peroxide [1] may be used as a good reagent for perfluoroalkylation of aromatic compounds.
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