Russian Chemical Bulletin p. 934 - 937 (1999)
Update date:2022-08-04
Topics:
Glushakova
Skorodumova
Nevodchikov
Abakumova
Makarenko
Cherkasov
Druzhkov
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.
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