Alkoxylation of 3,6-di-tert-butyl-1,2-benzoquinone. New bis-1,2-benzoquinones

Abstract

Alkoxylation of 3,6-di- tert -butyl-1,2-benzoquinone with a number of diols, including propane-1,3-diol, butane-1,4-diol, di-, and triethylene glycols, and cyclohexane-1,4-diyldimethanol, was studied. Nine new 4-alkoxy-3,6-di- tert -butyl-1,2-benzoquinones were synthesized, four of which were bis-1,2-benzoquinones with different tethers (6–13 atoms) between the quinone fragments. Depending on the length of the chain between the hydroxy groups in glycols, bicyclic 4,5-disubstituted 3,6-di- tert -butyl-1,2-benzoquinones were formed or their stepwise alkoxylation occurred. The newly synthesized o -benzoquinone derivatives can be reduced with alkali metals to give radical anions and converted into semiquinone chelates with manganese carbonyl.