Direct synthesis of fluorocarbon peroxides—II: The addition of fluoroperoxytrifluoromethane to alkenes

Abstract

FLUOROCARBON peroxides can now be obtained in considerable variety by the direct addition of the CF3OOgroup to suitable substrates. We have previously demonstrated the utility of trifluoromethyl hydroperoxide, CF3OOH[1--4], and bis(trifluoromethyl) trioxide, CF3OsCF315-7], in the direct synthesis of novel organic and inorganic peroxides. The reaction of CF303CF3 with alkenes gives rise to an interesting series of compounds of the type, CFsOOCR~R:CR2R4OCF3 and the method is quite general. In order to extend this kind of reaction to related derivatives containing only the peroxide linkage, we have investigated the reactions of fluoroperoxytrifluoromethane, CFsOOF and chloroperoxytrifluoromethane, CF3OOCI[8] with certain alkenes. These reagents can yield peroxides which differ only in the substitution of a fluorine by chlorine and along with the derivatives obtained with CF303CF3, allows one in principle to obtain a related series of peroxides of the general formulas CF3OOCRtR2CR3R4OCF3, CF3OOCRIR2CR3R4F and CF3OOCRMR2CR3R4CI. The addition of CF3OOF and CF3OOC1 to certain alkenes occurs readily at low temperatures according to the general equations