The formation and thermal decomposition of 4-hydroperoxy-2-hydroxy-3,4,6-triisopropylcyclohexa-2,5-dienone

Auto-oxidation of 3,4,6-triisopropylcatechol affords crystalline 2-hydroxy-4-hydroperoxy-3,4,6-triisopropylcyclohexa-2,5-dienone. Thermal decomposition of the resulting hydroperoxide was carried out and the reaction products were determined. The decomposition mainly proceeds by a route without cleavage of the O—O bond, unusual for hydroperoxides, to give the starting 3,4,6-triisopropylcatechol and 3,4,6-triisopropylbenzo-1,2-quinone. The hydroperoxide decomposes in part according to the traditional pattern involving the O—O bond cleavage to give 3-hydroxy-2,5-diisopropylbenzo-1,4-quinone.     

N- and O-arylation with triphenylantimony ortho-phenylenedioxides

2,2,2-Triphenyl-1,3,2-benzodioxastibolanes react with alcohols, phenols, and amines in the presence of copper salts to give the corresponding O- and N-phenyl derivatives. Cyclic Sb^V dialkoxide containing an electron-withdrawing nitro group in the dioxastibolane fragment is most reactive in N-phenylation of primary and secondary amines. Organoantimony analogs containing electron-donating groups are more efficient in O-phenylation of primary and secondary alcohols and phenols.