Organic peroxides. Part 12. The preparation and properties of some triazinyl peroxides
Abstract
The triazinyl peroxides (A; X = Y = OOBut; X = OMe, Y = OOBut; X = Y = OMe; X = NEt2, Y = OOBut; X = Y = NEt2) and (B) have been prepared from the reaction between the appropriate peroxidic nucleophile and chlorotriazine. The structures of the peroxides are confirmed by their 13C n.m.r. spectra, and by the recovery of t-butyl hydroperoxide when the peroxides (A; X = Y = OOBut; X = OMe, Y = OOBut) were hydrolysed. [graphic omitted]. These peroxides are thermally stable up to ca. 90 °C. Photolysis of the peroxides (A) gives the radical ButO· and XYC3N3O·. The e.s.r. spectra of the triazinoxyl radicals could not be observed, but the adducts XYC3N3OCH2CH2· and XYC3N3OP(OMe)3, which they form with ethylene and with trimethyl phosphite, respectively, were detected. It is suggested that these properties imply that the radicals have a σ-O rather than a π-delocalised structure.