The reaction 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 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.