The reactions of 3,6-di-tert-butyl-1,2-benzoquinone and 3,6-di-tert-butylcatechol with tert-butyl hydroperoxide

Article abstract of DOI:10.1007/BF02494640

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.