o-Alkyl- or o-aryl-benzenecarboxylic
acids and alcohols containing an aromatic ring are treated with
a (diacetoxyiodo)arene–iodine system to give the
corresponding cyclized products such as phthalide, benzocoumarin
and chromane derivatives in moderate to good yields via
the corresponding oxygen-centred radicals. For the carboxylic
acids, [bis(trifluoroacetoxy)iodo]benzene functions effectively,
while (diacetoxyiodo)benzene is effective for the alcohols.
Chromane and its derivatives are obtained as iodinated compounds
by hypoiodite species derived from (diacetoxyiodo)benzene and
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Journal of the Chemical Society, Perkin Transactions 1
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