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The phenyl σ-radical formed by reduction of aryl halides in an aprotic solvent undergoes efficient radical substitution on an adjacent benzene ring. Several examples of this cyclisation reaction are given. The reaction is appropriate for the synthesis of 6-membered aromatic rings where the two reacting phenyl groups are held in a cis-configuration by an olefin bond or another aromatic ring.
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Grimshaw et al. (1982) studied this question.
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