- Low-temperature oxidation of 3,6-di-tert-butyl-o-benzoquinone and 3,6-di-tert-butylpyrocatechol with tert-butyl hydroperoxide in the presence of aluminum, titanium, and zirconium tert-butylates
-
Systems consisting of metal (Al, Ti, Zr) tert-butylate and tert-butyl hydroperoxide oxidize 3,6-di-tert-butyl-o-benzoquinone under mild conditions (room temperature, benzene). With (t-BuO)3Al and (t-BuO) 4Zr, the major reaction products are 5-hydroxy-3,6-di-tert-butyl-2,3- epoxy-p-benzoquinone, and with (t-BuO)4Ti, 2-hydroxy-3,6-di-tert- butyl-p-benzoquinone. Under the conditions of this reaction, 3,6-di-tert-butylpyrocatechol initially transforms into 3,6-di-tert-butyl-o- benzoquinone. The reactions involve metalcontaining peroxides. Nauka/Interperiodica 2006.
- Stepovik,Gulenova,Shavyrin,Fukin
-
-
Read Online
- KINETICS AND MECHANISM OF THE REACTION OF OZONE WITH 3,6-DI-tert-BUTYLPYROCATECHOL
-
The reaction of ozone with 3,6-di-tert-butylpyrocatechol at ca. 20 deg C was investigated, and it was found that the main reaction product was 3,6-di-tert-butylquinone, while the reaction rate was proportional to the concentrations of the reagents.A react
- Konstantinova, M. L.,Vol'eva, V. B.,Razumovskii, S. D.
-
-
Read Online
- Reactions of hydroxyl-containing compounds with tert-butyl hydroperoxide in the presence of chromium tetra-tert-butoxide
-
Primary and secondary aliphatic, alkylaromatic, cyclic, and organoelement alcohols are efficiently oxidized by tert-butyl hydroperoxide in the presence of both equimolar and catalytic quantities of chromium tetra-tert-butoxide (C6H6, 20°C). α-Diols containing tertiary hydroxyl groups interact with this system via oxidative splitting of the carbon scaffold. The oxidation includes the stages of formation and decomposition of chromium-containing peroxy compounds. Further transformations of the carbonyl compounds depend on the structure of radicals in the molecules.
- Stepovik,Zaburdaeva,Fukin,Karaghiosoff
-
p. 2547 - 2559
(2015/12/30)
-
- Alkoxylation of 3,6-Di-tert-butyl-1,2-benzoquinone. New Bis-1,2-benzoquinones
-
Alkoxylation of 3,6-di-tert-butyl-1,2-benzoquinone with a number of diols, including propane-1,3- diol, butane-1,4-diol, di-, and triethylene glycols, and cyclohexane-1,4-diyldimethanol, was studied. Nine new 4-alkoxy-3,6-di-tert- butyl-1,2-benzoquinones were synthesized, four of which were bis-1,2-benzoquinones with different tethers (6-13 atoms) between the quinone fragments. Depending on the length of the chain between the hydroxy groups in glycols, bicyclic 4,5-disubstituted 3,6-di-tert-butyl-1,2-benzoquinones were formed or their stepwise alkoxylation occurred. The newly synthesized o-benzoquinone derivatives can be reduced with alkali metals to give radical anions and converted into semiquinone chelates with manganese carbonyl. Pleiades Publishing, Ltd., 2011.
- Shurygina,Druzhkov,Arsen'ev,Bubnov,Fukin,Chesnokov,Cherkasov
-
scheme or table
p. 486 - 495
(2011/07/08)
-
- Reaction of zirconium alkoxides with tert-butyl hydroperoxide. Oxidative ability of the Zr(OBu-t)4-t-BuOOH system
-
Oxidation of the isopropoxy group in the Zr(i-PrO)4·i- PrOH complex involves both direct reaction with tert-butyl hydroperoxide and intermediate formation of zirconium peroxy compound. Zirconium tetra-tert-butoxide reacts with tert-bytyl hydroperoxide to form metal-containing peroxide and trioxide. Decomposition of the latter leads to oxygen evolution and is accompanied by radical formation. The alkoxyl and peroxyl radicals formed were identified by ESR spectroscopy. The nature of the oxidant (oxygen, zirconium-containing peroxide and-trioxide) in the Zr(OBu-t)4-t-BuOOH system is determined by the structure of the substrate molecule. Pleiades Publishing, Inc., 2006.
- Gulenova,Stepovik,Cherkasov
-
p. 980 - 988
(2008/02/03)
-
- The reactions of 3,6-di-tert-butyl-1,2-benzoquinone and 3,6-di-tert-butylcatechol with tert-butyl hydroperoxide
-
Reaction of 3,6-di-tert-butyl-1,2-benzoquinone and 3,6-di-tert-butylcatechol with tert-butyl hydroperoxide in aprotlc solvents leads to the generation of semiquinone (SQ 'H), alkylperoxy (ROO'), and alkyloxy radicals. The reaction of SQ'H and ROO' produces 2,5-di-tert-butyl-6-hydroxy-1,4-benzoquinone, 3,6-di-tert-butyl-1-oxacyclohepta-3,5-diene2,7-dione, and 2,5-di-tert-butyl-3,6-dihydroxy-1,4-benzoquinone. The radical generated from solvent attacks SQ' H at position 4 with C-C bond formation. 4-Benzyl-2,5-di-tert-butyl-6-hydroxycyclohexa-2,5-diene-1-dione produced in this way is transformed into 4-benzyl-3,6-di-tert-butyl-1,2-benzoquinone under the reaction conditions.
- Glushakova,Skorodumova,Nevodchikov,Abakumova,Makarenko,Cherkasov,Druzhkov
-
p. 934 - 937
(2007/10/03)
-
- Hydroxylation of substituted diatomic phenols and their derivatives
-
Oxidation of 3,6-di-tert-butylpyrocatechol in protic media is accompanied by the formation of 3,6-di-tert-butyl-2-hydroxy-para-benzoquinone. Hydroxylation of the 3,5-isomer results in dealkylation and isomerization with the formation of 6-tert-butyl-2-hydroxypora-benzoquinone and the quinone mentioned above, respectively. Their ratio depends on the nature of the solvent. Analogous processes accompany redox transformations of 2,6-di-tert-butylhydroquinone, 2,6-diphenyl-para-benzoquinone, and 2,4,6-tri-tert-butylphenol adsorbed on silica gel. Derivatives of 3,5-substituted pyrocatechols formed under conditions of heterophase oxidation in air are capable of transformations to form nitrogen-containing compounds.
- Vol'eva,Prokof'eva,Belostotskaya,Komissarova,Ershov
-
p. 1952 - 1955
(2007/10/03)
-
- SYNTHESIS, STRUCTURE , AND PROPERTIES OF 2-(TRIPHENYLSTANNYLOXY)-3,6-DI-tert BUTYL-1,4-BENZOQUINONE
-
2-(Triphenylstannyloxy)-3,6-di-tert-butyl-1,4-benzoquinone (1) was obtained from the potassium salt of 3,6-di-tert-butyl-2-hydroxy-1,4-benzoquinone and triphenyltin bromide in methanol and characterized by x-ray diffraction analysis, electronic, IR, and NMR spectroscopy.According to x-ray diffraction data, the single crystal of 1 has the structure of a chain metal polymer with bridging hydroxy-para-quinone ligands; the coordination number of tin is six.Complex 1 is reduced by cobaltocene to the corresponding radical anion.In solutions, 1 reacts with metal-centered radicals SnPh3, PbPh3, and Mn(CO)5 with formation of paramagnetic binuclear ortho-semiquinone complexes. Keywords: 2-triphenylstannyloxy-3,6-di-tert-butyl-1,4-benzoquinone, synthesis, x-ray diffraction analysis, electronic absorption spectra, IR spectroscopy, NMR spectroscopy, reaction with radicals.
- Kabarova, N.Yu.,Cherkasov, V.K.,Zakharov, L.N.,Abakumov, G.A.,Struchkov, Yu.T.,Abakumova, L. G.
-
p. 2224 - 2229
(2007/10/02)
-
- REDOX REACTIONS OF 3,6-DI-TERT-BUTYL-ORTHO-BENZOQUINONE, CATALYZED BY TETRAFLUOROSILANE
-
Tetrafluorosilane-catalyzed redox reactions of 3,6-di-tert-butyl-ortho-benzoquinone have been examined.From the EPR spectroscopic data and a study of the reaction products, a mechanism for these reactions is proposed involving the formation of a quinone-tetrafluorosilane complex which has strong oxidizing properties, and which enables the original quinone to undergo further reactions.
- Chekalov, A. K.,Gvazava, N. G.,Vol'eva, V. B.,Prokof'eva, T. I.,Prokof'ev, A. I.,Ershov, V. V.
-
p. 991 - 993
(2007/10/02)
-