Synthesis of halogenated diphenyl ethers and dibenzofurans - A discussion of specific isomers available |
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Authors: | Anders Garå Kurt Andersson Carl-Axel Nilsson Ake Norström |
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Institution: | Department of Organic Chemistry Umeå University S-901 87 Umeå Sweden;National Board of Occupational Safety and Health Department of Occupational Health in Umeå Box 6104 S-900 06 Umeå Sweden |
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Abstract: | Synthetic routes for the preparation of halogenated diphenyl ethers and dibenzofurans are reviewed, and isomers reported in the literature are listed. In addition, the routes preferred for the synthesis of specific chlorinated isomers - especially from the point of view of an unambiguous structural assignment - are discussed in detail. The route recommended for chlorinated diphenyl ethers is the coupling of biaryliodonium salts with phenols, and for chlorinated dibenzofurans the palladium acetate-promoted cyclization of diphenyl ethers. Chlorinated isomers of diphenyl ethers and dibenzofurans which are available via these routes are listed. Furthermore, the synthesis of a new octachlorodiphenyliodonium salt and its coupling with three different chlorophenols are described, and the cyclization of an octachlorodiphenyl ether to octachlorodibenzofuran is shown. |
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