Issue 5, 1997

Formation and synthetic use of oxygen-centred radicals with (diacetoxyiodo)arenes

Abstract

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 iodine.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1997, 787-794

Formation and synthetic use of oxygen-centred radicals with (diacetoxyiodo)arenes

H. Togo, T. Muraki, Y. Hoshina, K. Yamaguchi<img border="0" src="https://www.rsc.org/images/entities/char_200a.gif" alt=" " xmlns="http://www.rsc.org/schema/rscart38" /> and M. Yokoyama<img border="0" src="https://www.rsc.org/images/entities/char_200a.gif" alt=" " xmlns="http://www.rsc.org/schema/rscart38" />, J. Chem. Soc., Perkin Trans. 1, 1997, 787 DOI: 10.1039/A603446B

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