The integral role of halide ions as a ligand in the reactions of stoichiometric arylpalladiumreagents and Pd(II)-catalyzed reaction of phenylmercuric acetate with various allyliccompounds were studied. The halide ion was found to inhibit
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-H elimination and promote
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-heteroatom elimination in acidic media. In this reaction, a C-Pd intermediate with a
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-heteroatom (including halogen, acetoxy, alkoxy, and hydroxyl groups) gives only
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-heteroatom elimination product in the presence of halide ions, while
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-H elimination is effectivelyblocked.