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o-(Prop-2-enyloxy)phenyl lead triacetate 6, which was obtained by treatment of the corresponding boronic acid with lead tetraacetate, has been shown to react with iodide and azide ions, 2,4,6-trimethyl phenol, ethyl 2-oxocyclopentanecarboxylate, and the sodium salt of 2-nitropropane to give only those products which, in a formal sense, are derived by direct nucleophilic displacement of the Pb(OAc)3 group. The complete absence of 3-substituted dihydrobenzofurans among the products is strong evidence that aryl free radicals are not involved in the arylation reactions of aryllead triacetates.
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Morgan et al. (1993) studied this question.
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