title: Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides.
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.
authors.affiliation: Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK. eman.zawia@hud.ac.uk.
authors.forename: Eman
authors.initials: E
authors.lastname: Zawia
authors.affiliation: Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK. w.j.moran@hud.ac.uk.
authors.forename: Wesley J
authors.initials: WJ
authors.lastname: Moran
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D014752:Vinyl Chloride / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D009861:Onium Compounds; D012492:Salts; D014752:Vinyl Chloride; D004121:Dimethyl Sulfoxide
keywords: hypervalent iodine; iodonium salt; solvolysis; substitution