Abstract
Mechanistic implications of
the ready formation of aryl iodides from aryldiazonium
salt solutions and the iodide ion (in contrast with the general need for
cuprous or other catalysts with other halides) have been studied. The reaction
between benzenediazonium fluoroborate
and potassium iodide in methanol at 0�C has been investigated. A new mechanism
involving initial one-electron transfer from the iodide anion to the benzenediazonium cation, resulting in the formation of
radical intermediates by heterolytic cleavage of a bond, has been proposed in order
to account for the products, viz. iodobenzene,
benzene, biphenyl, iodine, anisole, and formaldehyde, and the effect of
photochemical catalysis.
Cited by
33 articles.
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