33521-88-9Relevant academic research and scientific papers
Synthesis of alkenyl sulfides through the iron-catalyzed cross-coupling reaction of vinyl halides with thiols
Lin, Yun-Yung,Wang, Yu-Jen,Lin, Che-Hung,Cheng, Jun-Hao,Lee, Chin-Fa
, p. 6100 - 6106 (2012/10/08)
We report here the iron-catalyzed cross-coupling reaction of alkyl vinyl halides with thiols. While many works are devoted to the coupling of thiols with alkyl vinyl iodides, interestingly, the known S-vinylation of vinyl bromides and chlorides is limited
Efficient copper-catalyzed s-vinylation of thiols with vinyl halides
Kao, Hsin-Lun,Lee, Chin-Fa
supporting information; experimental part, p. 5204 - 5207 (2011/12/04)
The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couplewith aryl iodides in the presence of only 0.5mol% Cu2O without the need for an ancillary liga
Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides
Sacasa, Pablo R.,Zayas, Jessica,Wnuk, Stanislaw F.
experimental part, p. 5424 - 5427 (2009/12/06)
Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.
A simplified preparation of vinyl sulfides, selenides and tellurides by a Wittig-type reaction
Silveira, Claudio C.,Begnini, Mauro L.,Boeck, Paula,Braga, Antonio L.
, p. 221 - 224 (2007/10/03)
The preparation of several vinyl sulfides, selenides and tellurides by Wittig-type reaction in a one-pot procedure is described. The chalcogenyl triphenylphosphoranes 3 are formed 'in situ' by the reaction of chloromethyl phenyl chalcogenide, potassium tert-butoxide and triphenylphosphine. Reaction of 3 with carbonyl compounds affords the vinyl chalcogenides 6-9 with preferential Z-configuration.
Hole transfer promoted hydrogenation: One-electron oxidation as a strategy for selective reduction of π-bonds
Mirafzal, Gholam A.,Liu, Jianping,Bauld, Nathan L.
, p. 6072 - 6077 (2007/10/02)
One-electron oxidation is developed as a strategy for selective and efficient reduction of relatively ionizable functionalities, including conjugated dienes, styrenes, vinyl sulfides, aromatics, and even strained σ-bonds. Reduction is highly sensitive to substrate ionizability and permits selective reduction of the more ionizable function in a difunctional context. Ionization of the substrates to cation radicals is effected via the mild hole transfer agent tris(4-bromophenyl)aminium hexachloroantimonate, and subsequent reduction of the cation radicals is accomplished by tributyltin hydride. The new reduction conditions provide a novel route for generating free radicals which may prove useful in the field of radical cyclizations. This is especially attractive in the case of phenyl vinyl sulfides since the phenylthio group, which remains intact subsequent to cyclization, provides versatile functionality for further synthetic operations.
THE REACTION OF ALKYL PHENYL SULPHIDES WITH MANGANESE DIOXIDE AND ACETYL CHLORIDE
Bellesia, Franco,Ghelfi, Franco,Pagnoni, Ugo Maria,Pinetti, Adriano
, p. 289 - 291 (2007/10/02)
In a one-pot reaction, manganese dioxide in stoichiometric amounts and acetyl chloride transform alkyl phenyl sulphides into the corresponding 1-alkenyl phenyl sulphides; these latter products can be undergo chlorination of the double bond promoted by the
A New Version of the Peterson Olefination Using Bis(trimethylsilyl)methyl Derivatives and Fluoride Ion as Catalyst
Palomo, Claudio,Aizpurua, Jesus M.,Garcia, Jesus M.,Ganboa, Inaki,Cossio, F. P.,et al.
, p. 2498 - 2503 (2007/10/02)
Reaction between a variety of bis(trimethylsilyl)methyl derivatives and carbonyl compounds under fluoride ion as catalyst is described.The reaction works especially well with nonenolizable carbonyl compounds to give the expected alkenes in high yields and, in some cases, with high stereoselectivity.Application of this methodology to an intramolecular alkenation providing a tricyclic benzocarbacephem ring system is also described.
THIOPHENOL PROMOTED CYCLIZATION OF ENYNES
Broka, Chris A.,Reichert, David E. C.
, p. 1503 - 1506 (2007/10/02)
Vinyl radicals generated by the addition of thiophenol to enynes have been shown to cyclize regioselectively giving cyclohexylidene thioethers.
ELIMINATIVE DEOXYGENATION OF SUBSTITUTED-α-HALOSULFOXIDES
Reutrakul, Vichai,Poochaivatananon, Patcharin
, p. 531 - 534 (2007/10/02)
The reaction of substituted-α-halosulfoxides with TiCl4-Zn in ether gave the corresponding phenyl vinyl sulfides in good yields.
