Aqueous DMSO mediated conversion of (2-(arylsulfonyl)vinyl)iodonium salts to aldehydes and vinyl chlorides

Eman Zawia, Wesley J. Moran

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

LanguageEnglish
Article number1073
Number of pages11
JournalMolecules
Volume21
Issue number8
DOIs
Publication statusPublished - 16 Aug 2016

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Vinyl Chloride
Dimethyl Sulfoxide
aldehydes
Aldehydes
Salts
chlorides
salts
Bearings (structural)
solvolysis
Synthetic Chemistry Techniques
chemistry
synthesis

Cite this

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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.",
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Aqueous DMSO mediated conversion of (2-(arylsulfonyl)vinyl)iodonium salts to aldehydes and vinyl chlorides. / Zawia, Eman; Moran, Wesley J.

In: Molecules, Vol. 21, No. 8, 1073, 16.08.2016.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Zawia, Eman

AU - Moran, Wesley J.

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Y1 - 2016/8/16

N2 - 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.

AB - 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.

KW - Hypervalent iodine

KW - Iodonium salt

KW - Solvolysis

KW - Substitution

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DO - 10.3390/molecules21081073

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T2 - Molecules

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