Reactions of organic peroxides. Part XX. Peroxides from bicycloalkyl-2,2′-diones and hydrogen peroxide

Abstract

Treatment of the bicycloalkyl-2,2′-diones obtained from oxidation by nickel peroxide of cyclopentanone, cyclohexanone, 4-methylcyclohexanone, and cycloheptanone with hydrogen peroxide afforded the corresponding symmetrical dihydroxy-peroxides (3,6-dihydroxy-1,2-dioxans). Perhydrodibenzo[c,e][1,2]dioxin-4a,6a-diol gave (i) mainly dodec-6-enedioic acid on reaction with iron (II) sulphate, (ii) the same acid, together with branched-chain dicarboxylic acids, on photolysis, and (iii) a mixture of lactones from treatment with formic acid. Bicyclohexyl-2,2′-dione and t-butyl hydroperoxide yielded a symmetrical bis-t-butylperoxyperhydrodibenzofuran.