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Molecules 2016, 21(8), 1073; doi:10.3390/molecules21081073

Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides

Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK
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Academic Editor: Derek J. McPhee
Received: 20 July 2016 / Revised: 4 August 2016 / Accepted: 6 August 2016 / Published: 16 August 2016
(This article belongs to the Special Issue Hypervalent Iodine Chemistry)
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Abstract

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. View Full-Text
Keywords: hypervalent iodine; iodonium salt; solvolysis; substitution hypervalent iodine; iodonium salt; solvolysis; substitution
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Zawia, E.; Moran, W.J. Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides. Molecules 2016, 21, 1073.

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