Abstract
Reaction of 3,6-di-tert-butyl-1,2-benzoquinone and 3,6-di-tert-butylcatechol withtert-butyl hydroperoxide in aprotic 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-diene-2,7-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.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 943–946, May, 1999.
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Glushakova, V.N., Skorodumova, N.A., Nevodchikov, V.I. et al. The reaction of 3,6-di-tert-butyl-1,2-benzoquinone and 3,6-di-tert-butylcatechol withtert-butyl hydroperoxide. Russ Chem Bull 48, 934–937 (1999). https://doi.org/10.1007/BF02494640
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DOI: https://doi.org/10.1007/BF02494640