90020-44-3Relevant academic research and scientific papers
Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides
Sacasa, Pablo R.,Zayas, Jessica,Wnuk, Stanislaw F.
scheme or table, 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.
Preparation and reaction of phenylsulfonyl-substituted dizinciomethane
Baba, Yoko,Toshimitsu, Akio,Matsubara, Seijiro
, p. 864 - 865 (2008/02/12)
Treatment of dibromomethyl phenyl sulfone with zinc powder in the presence of a catalytic amount of lead in THF afforded phenylsulfonyl-substituted dizinciomethane. The species converts a ketone or aldehyde into an alkenyl sulfone via a Wittig-type olefination reaction with the assistance of β-TiCl3. Copyright
Radical-mediated silyl- and germyldesulfonylation of vinyl and (α-fluoro)vinyl sulfones: Application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings
Wnuk, Stanislaw F.,Garcia Jr., Pedro I.,Wang, Zhizhong
, p. 2047 - 2049 (2007/10/03)
Equation presented. Radical-mediated silyl- and germyldesulfonylations of various vinyl and (α-fluoro)vinyl sulfones with tris(trimethylsilyl)silane and germanium hydrides provide access to vinyl and (α-fluoro)vinyl silanes and germanes. Upon oxidative treatment with hydrogen peroxide in basic aqueous solution, the vinyl tris(trimethylsilyl)silanes and -germanes undergo Pd-catalyzed cross-couplings with aryl halides.
Samarium(II) iodide-mediated deoxygenative debromination of α-bromo-β-hydroxy (acetoxy) phenyl sulfones: Synthesis of α,β-unsaturated sulfones
Reutrakul, Vichai,Jarussophon, Suwatchai,Pohmakotr, Manat,Chaiyasut, Yupa,U-Thet, Saengvimon,Tuchinda, Patoomratana
, p. 2285 - 2288 (2007/10/03)
Deoxygenative debromination of α-bromo-β-hydroxy (acetoxy) phenyl sulfones with samarium(II) iodide led to substituted α,β-unsaturated sulfones in good to excellent yields. The E-isomer is the major product. A possible mechanism via an α-sulfonyl radical pathway is proposed.
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.
Synthesis of Alkenes via Peterson Reaction
Ager, David J.
, p. 183 - 194 (2007/10/02)
The α-phenylthiosilanes (2) have been used to prepare the α-silyl anions (1) by reaction with lithium naphthalenide; subsequent condensation with a carbonyl compound gave the alkene (8) via the Peterson reaction.The α-phenylthiosilanes (2) were prepared from n,n-bis(phenylthio)acetals (4) by reaction with lithium naphthalenide and chlorotrimethylsilane.The n,n-bis(phenylthio)acetals (4) were obtained, in turn, from 1,1-bis(phenylthio)acetals (5) by anion formation with butyl-lithium-N,N,N',N'-tetramethylethylenediamine complex in hexane followed by reaction with an alkyl halide.The Peterson reaction was also used to prepare vinyl sulphides (9) and vinyl sulphones (13).
Preparation of Vinylic Sulphones by Peterson Olefination using Phenyl Trimethylsilylmethyl Sulphone
Craig, Donald,Ley, Steven V.,Simpkins, Nigel S.,Whitham, Gordon H.,Prior, Michael J.
, p. 1949 - 1952 (2007/10/02)
The anion generated from phenyl trimethylsilylmethyl sulphone using butyl-lithium in dimethoxyethane, readily reacts at -78 deg C with various carbonyl compounds to afford vinylic sulphones on work-up at room temperature.The reaction conditions are tolera
IODOMETHYL PHENYL SULFOXIDE: REACTIVITY AND SYNTHETIC APPLICATIONS
Reutrakul, Vichai,Panyachotipun, Chitchanun,Hahnvajanawong, Viwat,Sotheeswaran, S.
, p. 1825 - 1828 (2007/10/02)
Lithio iodomethyl phenyl sulfoxides reacted with alkyl halides and carbonyl compounds to give adducts in good to moderate yields.Solvolysis of the carbonyl adducts led to sulfones or the ring expanded product.
Reactions of α-Silylsulphones
Ager, David J.
, p. 486 - 488 (2007/10/02)
α-Silylsulphones have been utilised to prepare vinylsulphones via the Peterson reaction and ketones by alkylation, reduction, and sila-Pummerer rearrangement.
Peterson Olefination using Phenylsulphonyltrimethylsilylmethane. A New Preparation of Vinylic Sulphones
Ley, Steven V.,Simpkins, Nigel S.
, p. 1281 - 1282 (2007/10/02)
The anion from phenylsulphonyltrimethylsilylmethane reacts, in 1,2-dimethoxyethane at -78 deg C, with both aldehydes and ketones to give the corresponding alkenyl phenyl sulphones in good yield.
