Polarographic studies of the three isomeric dibromobenzenes and bromochlorobenzenes have been carried out in acetonitrile and dimethylformamide. The results with o ‐dibromobenzene in these solvents point to an intermediate which eliminates a bromide ion and forms benzyne. The intermediate from o ‐bromochlorobenzene under the same conditions undergoes partial elimination to benzyne. The elimination reaction also occurs to a slight extent for o ‐dibromobenzene in aqueous dioxane. The formation of benzyne was verified by a large‐scale electrolytic reduction of o ‐dibromobenzene in dimethylformamide in the presence of furan. The tarry product obtained on acid hydrolysis gave a 1 % yield of α‐naphthol.
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Wawzonek et al. (1963) studied this question.