Aromatic systems protonated benzyl methyl

Addition of 0- to double bonds and to aromatic systems was found to be quite slow. Simic et al. (1973) found that O- reacts with unsaturated aliphatic alcohols, especially by H-atom abstraction. As compared to O, HO reacts more rapidly (by two to three times) with the same compounds. In the case of 1,4-benzoquinone, the reaction with O consists of the hydrogen double abstraction and leads to the 2,3-dehydrobenzoquinone anion-radical (Davico et al. 1999, references therein). Christensen et al. (1973) found that 0- reacts with toluene in aqueous solution to form benzyl radical through an H-atom transfer process from the methyl group. Generally, the O anion-radical is a very strong H-atom abstractor, which can withdraw a proton even from organic dianions (Vieira et al. 1997). 

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