Potassium 4-iodylbenzenesulfonate: preparation, structure, and application as a reagent for oxidative iodination of arenes
| Parent link: | European Journal of Organic Chemistry Vol. 2012, iss. 30.— 2012.— [P. 5935-5942] |
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| Autor Corporativo: | |
| Outros autores: | , , , , , , |
| Summary: | Title screen A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by the oxidation of 4-iodobenzensulfonic acid with Oxone in water. This potassium salt can be further converted into 4-iodylbenzenesulfonic acid by treatment with the acidic form of Amberlyst 15 in water. A single-crystal X-ray structure of potassium 4-iodylbenzenesulfonate revealed the presence of polymeric chains in the solid state due to a combination of numerous intra- and intermolecular interactions. Potassium 4-iodylbenzenesulfonate will likely find many practical applications as a thermally stable and water-soluble hypervalent iodine-based oxidant, particularly useful as a reagent for oxidative iodination of aromatic substrates. This reagent can be effectively recovered from the reaction mixture (92 % recovery) by treatment of the aqueous layer with Oxone at 60 °C for 2 h, followed by filtration of the precipitate. |
| Idioma: | inglés |
| Publicado: |
2012
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| Subjects: | |
| Acceso en liña: | http://dx.doi.org/10.1002/ejoc.201201064 |
| Formato: | Electrónico Capítulo de libro |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=650194 |
| Summary: | Title screen A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by the oxidation of 4-iodobenzensulfonic acid with Oxone in water. This potassium salt can be further converted into 4-iodylbenzenesulfonic acid by treatment with the acidic form of Amberlyst 15 in water. A single-crystal X-ray structure of potassium 4-iodylbenzenesulfonate revealed the presence of polymeric chains in the solid state due to a combination of numerous intra- and intermolecular interactions. Potassium 4-iodylbenzenesulfonate will likely find many practical applications as a thermally stable and water-soluble hypervalent iodine-based oxidant, particularly useful as a reagent for oxidative iodination of aromatic substrates. This reagent can be effectively recovered from the reaction mixture (92 % recovery) by treatment of the aqueous layer with Oxone at 60 °C for 2 h, followed by filtration of the precipitate. |
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| DOI: | 10.1002/ejoc.201201064 |