Antiradical activity of dioxolane derivatives

1,3-Benzodioxoles synthesized by condensation of 3,6-di-tert-butylbenzene-1,2-diol with carbonyl compounds showed antiradical activity due to their ability to undergo one-electron oxidation with formation of stable radical cations. On this basis, the antiknock effect of their structural analogs, 1,3-dioxolanes derived from vicinal diols, was interpreted in terms of oxidation of these compounds with active radicals generated from fuel hydrocarbons to produce more stable radical or radical ion species, depending on the fuel composition. The formation of radical species was detected in model oxidation reactions of 2,2-dimethyl-1,3-dioxolane and 2,2-dimethyl-1,3-dioxolan-4-ylmethanol with radicals generated by photolysis of iron(III) chloride and benzoyl peroxide.     

Isotopic Study of the Formation of Phenoxazine Derivatives in the Transformations of 3,5-Di-tert-Butylcatechol Adsorbed in Thin SiO2-nTiO2 Layers in the Air

A study was carried out on the isotopic composition of the tetra-tert-butylphenoxazine derivatives formed in the heterophase transformations of 3,5-di-tert-butylcatechol adsorbed on thin SiO2 layers with microscopic traces of Ti and Mn in a nitrogen-oxygen atmosphere enriched with ¹⁵N₂. The formation of isotopically-labeled tetra-tert-butylphenoxazinyl and hydroxytetra-tert-butylphenoxazinyl radicals and tetra-tert-butylphenoxazinone indicated the participation of atmospheric nitrogen in the heterophase catalytic reaction.     

Reaction of sterically hindered phenol toluenesulfonates with nucleophilic reagents

Conclusions The reactions of 4-hydroxy-3,5-di-tert-butylphenylethyl, 4-hydroxy-3,5-di-tert-butylphenylisobutyl, and 4-hydroxy-3,5-di-tert-butylphenylmethoxyethyl toluenesulfonates with nucleophilic reagents were investigated.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2406–2408, October, 1970.     

Semi-hindered phenols. 1. Synthesis of 3,5-di-tert-butylsalicylic aldehyde

Some differences were observed in the solid- and liquid-phase benzylic oxidation of 2-(hydroxy- or dialkylamino)-methyl-4,6-di-tert-butylphenols. Oxidation of these semi-hindered phenols with lead tetraacetate gave a new compound: 3,5-di-tert-butyl-ortho-benzoquinone diacylal.N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 117977 Moscow. Institute of Synthetic Polymeric Materials, Russian Academy of Sciences, 117393 Moscow. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 10, pp. 2380–2384, October, 1992.     

Hybrid macromolecular antioxidants based on hydrophilic polymers and sterically hindered phenols

A novel class of biologically active substances was created. These are hybrid macromolecular antioxidants (HMAO) based on hydrophilic polymers with chemically grafted sterically hindered phenols with different structural parameters. The antiradical activities of HMAO were assessed in reactions with 2,2-diphenyl-1-picrylhydrazyl and the corresponding sodium sulfonate in various solvents. The mechanism that explains the substantially enhanced activities of HMAO in water was proposed. The state of HMAO in solutions was studied by viscosimetry and photon correlation spectroscopy. HMAO were assayed in biological models. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 751–760, April, 2007.     

The solid-phase catalytic oxydation of 2-hydroxy-3,5-di-tert-butylbenzyl alcohol

The solid-phase catalytic oxidation in the 2-hydroxy-3,5-di-tert-butylbenzyl alcohol-MnO₂-NaOH system to yield 2-hydroxy-3,5-di-tert-butylbenzaldehyde was carried out. Gaseous oxygen participates in the regeneration of the active form of the oxidant.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1833–1834, October, 1994.This work was carried out with the financial support of the Russian Foundation for Basic Research (Project No. 94-03-08653).