Condensations of benzil with phenols and aryl ethers mediated by tin(IV) chloride pentahydrate

The reaction of benzil with phenol at 180°C in the presence of SnCl 4·5H 2O produces a benzofuran, a benzofuranol, a benzodifuran, and a benzofuranone. Anhydrous tin(IV) chloride also gives a benzofuranofuranone. Other phenols and their methyl ethers yield related products. The good yields of the be...

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Bibliographic Details
Published in:Tetrahedron 2002-05, Vol.58 (21), p.4255-4260
Main Authors: Morrison, Brian J, Musgrave, Oliver C
Format: Article
Language:English
Subjects:
benzofurans
diones
furanones
phenols
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Summary:The reaction of benzil with phenol at 180°C in the presence of SnCl 4·5H 2O produces a benzofuran, a benzofuranol, a benzodifuran, and a benzofuranone. Anhydrous tin(IV) chloride also gives a benzofuranofuranone. Other phenols and their methyl ethers yield related products. The good yields of the benzo- and naphtho-furanones make the method an attractive alternative to the benzilic acid route to such compounds. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00357-5