Sodium iodide-mediated synthesis of vinyl sulfides and vinyl sulfones with solvent-controlled chemical selectivity

Solvent-controlled selectivity of the elimination/coupling reaction was realized for divergent synthesis of vinyl sulfides and vinyl sulfones. The described protocol is more convenient for the preparation of vinyl sulfide and vinyl sulfone related skeletons.

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Stereo- and Regiospecific Cu-Catalyzed Cross-Coupling Reaction of Vinyl Iodides and Thiols: A Very Mild and General Route for the Synthesis of Vinyl Sulfides

Organic Letters ◽

10.1021/ol801149n ◽

2008 ◽

Vol 10 (15) ◽

pp. 3363-3366 ◽

Cited By ~ 50

Author(s):

M. Shahjahan Kabir ◽

Michael L. Van Linn ◽

Aaron Monte ◽

James M. Cook

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Cross Coupling Reaction ◽

Vinyl Sulfides ◽

Vinyl Iodides

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ChemInform Abstract: Stereo- and Regiospecific Cu-Catalyzed Cross-Coupling Reaction of Vinyl Iodides and Thiols: A Very Mild and General Route for the Synthesis of Vinyl Sulfides.

ChemInform ◽

10.1002/chin.200847050 ◽

2008 ◽

Vol 39 (47) ◽

Author(s):

M. Shahjahan Kabir ◽

Michael L. Van Linn ◽

Aaron Monte ◽

James M. Cook

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Cross Coupling Reaction ◽

Vinyl Sulfides ◽

Vinyl Iodides

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Heck Vinylations Using Vinyl Sulfide, Vinyl Sulfoxide, Vinyl Sulfone, or Vinyl Sulfonate Derivatives and Aryl Bromides Catalyzed by a Palladium Complex Derived from a Tetraphosphine

Synthesis ◽

10.1055/s-2006-950244 ◽

2006 ◽

Vol 2006 (20) ◽

pp. 3495-3505 ◽

Cited By ~ 5

Author(s):

Henri Doucet ◽

Maurice Santelli ◽

Ahmed Battace ◽

Touriya Zair

Keyword(s):

Palladium Complex ◽

Vinyl Sulfone ◽

Vinyl Sulfide ◽

Aryl Bromides

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One electron transfer reaction of phenyl vinyl sulfides with dioxygen. The fate of the intermediate vinyl sulfide radical cations.

Tetrahedron Letters ◽

10.1016/s0040-4039(00)73645-8 ◽

1993 ◽

Vol 34 (22) ◽

pp. 3595-3598 ◽

Cited By ~ 2

Author(s):

Luisa Benati ◽

Pier Carlo Montevecchi ◽

Daniele Nanni ◽

Piero Spagnolo

Keyword(s):

Electron Transfer ◽

Transfer Reaction ◽

Radical Cations ◽

Electron Transfer Reaction ◽

Vinyl Sulfide ◽

Vinyl Sulfides ◽

Phenyl Vinyl

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Vinyl sulfide hydrolysis

Canadian Journal of Chemistry ◽

10.1139/v77-076 ◽

1977 ◽

Vol 55 (3) ◽

pp. 548-551 ◽

Cited By ~ 23

Author(s):

Robert A. McClelland

Keyword(s):

Double Bond ◽

Proton Transfer ◽

Acid Solutions ◽

Vinyl Ethers ◽

Vinyl Sulfide ◽

Carbonium Ion ◽

Carbon Double Bond ◽

Carbonium Ions ◽

Vinyl Sulfides ◽

Hydrolysis Of

The hydrolysis of vinyl sulfides in acid solutions is shown to proceed via a mechanism analogous to that of vinyl ethers, with slow proton transfer to the carbon–carbon double bond to produce a sulfur stabilized carbonium ion. Relative rates of hydrolysis of compounds RXCH=CH2 are CH3S—, 41; CH3O—, 1500; C6H5S—, 1; and C6H5O—, 10.5. This order is compared with that of other systems which produce similar stabilized carbonium ions.

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