Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides
Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual p...
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| Format: | Article |
| Language: | English |
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MDPI AG
2016-08-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/8/1073 |
| _version_ | 1818019723964579840 |
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| author | Eman Zawia Wesley J. Moran |
| author_facet | Eman Zawia Wesley J. Moran |
| author_sort | Eman Zawia |
| collection | DOAJ |
| description | Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides. |
| first_indexed | 2024-04-14T07:56:06Z |
| format | Article |
| id | doaj.art-e04029bd38c6412f942a089b9c3551f3 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-14T07:56:06Z |
| publishDate | 2016-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e04029bd38c6412f942a089b9c3551f32022-12-22T02:05:03ZengMDPI AGMolecules1420-30492016-08-01218107310.3390/molecules21081073molecules21081073Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl ChloridesEman Zawia0Wesley J. Moran1Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UKDepartment of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UKVinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides.http://www.mdpi.com/1420-3049/21/8/1073hypervalent iodineiodonium saltsolvolysissubstitution |
| spellingShingle | Eman Zawia Wesley J. Moran Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides Molecules hypervalent iodine iodonium salt solvolysis substitution |
| title | Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides |
| title_full | Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides |
| title_fullStr | Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides |
| title_full_unstemmed | Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides |
| title_short | Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides |
| title_sort | aqueous dmso mediated conversion of 2 arylsulfonyl vinyl iodonium salts to aldehydes and vinyl chlorides |
| topic | hypervalent iodine iodonium salt solvolysis substitution |
| url | http://www.mdpi.com/1420-3049/21/8/1073 |
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