Reaction of phenyllithium with 3,5-Di-tert-butyl-o-benzoquinone (TBQ) and structure of Li+(3,5-di-tert-butyl-o-seminiquinonate anion) in solution

Reactions between three groups of substituted o-quinones, 3,5-di-tert-butyl-1,2-benzoquinone (TBQ), 1,2-naphthoquinone, and 9,10-phenanthrenequinone, with an organometallic compound, phenyllithium, were investigated by electron paramagnetic resonance (EPR) spectrometry. The results revealed the formation of M(TBSQ) and the adduct Li(TBSQ)2,2'-bipyridine. There were also evidence for the formation of biphenyl from the oxidation of phenyllithium.