Mechanism of arylation of nucleophiles by aryllead triacetates. Part 1. Exclusion of a pathway involving aryl free radicals

Abstract

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.