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-butylcatecho l with tert-butyl hydroperoxide in aprotic solvents leads to the generation of semiquinone (SQ(.)H), alkylperoxy (ROO.), and alkyloxy radicals. The re action of SQ(.)H and ROO. produces 2, 5-di-tert-butyl-6-hydroxy-1,4-benzoqu inone, 3,6-di-tert-butyl-1-oxacyclohepta-3, 5-diene-2,7-dione, and 2,5-di-t ert-butyl-3,6-dihydroxy-1,4-benzoquinone, The radical generated from solven t attacks SQ(.)H at position 4 with C-C bond formation. 4-Benzyl-2,5-di-ter t-butyl-6-hydroxycyclohexa-2,5-diene-1-dione produced in this way is transf ormed into 4-benzyl-3,6-di-tert-butyl-1,2-benzoquinone under the reaction c onditions.