24422-74-0

Upstream product

• 40390-78-1 [(1-phenylethyl)thio]benzene 
• 49833-32-1 1-phenyl-1-(phenylsulfinyl)-ethene 
• 7417-81-4 benzyl phenyl sulfoxide 
• 74-88-4 methyl iodide 
• 98-80-6 phenylboronic acid 
• 6099-23-6 1-(phenylsulfinyl)acetophenone 
• 585-71-7 (1-bromoethyl)benzne 
• 108-98-5 thiophenol 
• 67300-99-6 1-phenylethenylmagnesium bromide 
• 670-98-4 methyl benzenesulfinate 
• 51207-25-1 ethylphenylsulfoxide 
• 26910-34-9 α-Bromoethyl phenyl sulfoxide 

Downstream Products

• 1859-03-6 ethyl benzenesulfinate 
• 100-42-5 styrene 
• 882-33-7 diphenyldisulfane 
• 16336-45-1 α-phenylthiostyrene 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 98-85-1 1-Phenylethanol 
• 1208-20-4 S-phenyl benzenethiosulfinate 

Relevant academic research and scientific papers

A route to benzylic arylsulfoxides from β-ketosulfoxides

The K2CO3-mediated benzylation of β-ketosulfoxides 4 with 2.0?equiv of benzylic halides 5 affords benzylic arylsulfoxides 6 in moderate yields along with trace amounts of chalcones 7. The products 6 are assumed to form in situ intermediates of sulfenate anions from β-ketosulfoxides which are commonly involved in carbon–sulfur bond formation. A plausible mechanism has been proposed.

Highly selective 30% hydrogen peroxide oxidation of sulfides to sulfoxides using micromixing

The highly selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide has been achieved under catalyst-free conditions using a T-shaped micromixer. The Royal Society of Chemistry.

Palladium-catalyzed suzuki-miyaura reaction involving a secondary sp 3 carbon: Studies of stereochemistry and scope of the reaction

Palladium-catalyzed C-C bond formation involving secondary sp 3-hybridized carbon is described. These reactions occur with secondary 1-bromoethyl arylsulfoxides and different arylboronic acids, to produce the corresponding arylated sulfoxides in moderate to high yields and with complete stereospecificity. Despite the presence of β hydrogens in the substrate, the competitive β-hydride elimination is not a significant side reaction when coordinating solvents are used. The reported cross-coupling involves secondary Csp3-Csp2 bond formation: this is the first time that a mechanistic study has been carried out with such substrates. The reaction proceeds with inversion of configuration at the stereogenic C sp3 carbon. The high stereospecificity of the coupling and the mildness of the reaction conditions allow for the preservation of the optical purities of reagents and products and the preparation of useful chiral targets.

Reaction of singlet oxygen with some benzylic sulfides

Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, α-methylbenzyl, and cumyl sulfides. Their contributions depend on the steric hindering around the sulfur atom. In protic solvents, the sulfoxide is the main product via a hydrogen-bonded persulfoxide. In apolar solvents, intramolecular α-H abstraction leads to oxidative C-S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.

Efficient and selective sulfoxidation by hydrogen peroxide, using a recyclable flavin-[BMIm]PF6 catalytic system

A new flavin catalyst 2 immobilized in an ionic liquid ([BMIm]PF 6) was used for the highly selective oxidation of sulfides to sulfoxides by hydrogen peroxide. The sulfoxides were obtained in good to high yields and high selectivity without any

Palladium-catalyzed reaction of boronic acids with chiral and racemic α-bromo sulfoxides

Palladium-catalyzed cross-coupling reactions of racemic α-bromo sulfoxides with boronic acids are carried out in either aqueous or nonaqueous medium with formation of a new C sp3-C sp2 bond. The arylation of chiral α-bromo sulfoxides occurs without racemization. The cross-coupling reaction is general and gives high yields with arylboronic acids substituted with either donor or acceptor groups but gives poor results with heteroarylboronic acids. The best yields are obtained using degassed solvents and CsF instead of aqueous base. The use of aqueous base and the presence of oxygen favor the homocoupling side reaction.

Unprecedented palladium-catalyzed cross-coupling reaction of α-bromo sulfoxides with boronic acids

(Matrix presented) A new Suzuki-type palladium-catalyzed reaction of boronic acids with α-bromo sulfoxides has been developed using a protocol similar to the well-documented reaction of boronic acids with aryl halides. Both cross-coupling and homocoupling processes were observed. The best yields in cross-coupling products were obtained when the presence of oxygen was carefully excluded using degassed solvents. The oxidative addition palladium complex intermediate could be isolated and characterized by X-ray single-crystal diffraction.

Origin of the Stereoselectivity in (Ethoxycarbonyl)-, Cyano-, and Phenyl-Substituted (Arylsulfinyl)methyl Radicals

An explanation for the very high diastereoselectivity observed for the reactions of carbonyl-substituted (arylsulfmyl)methyl radicals is presented, based on experimental results and semiempirical calculations. The influence of dipole-dipole interactions, allylic 1,3-strain(A1,3 strain), allylic 1,2-strain (A1,3 strain), and coulombic interactions is discussed based on stereoselectivities observed with (alkoxycarbonyl)-, cyano-, and aryl-substituted (arylsulfinyl)methyl radicals. In the second part, the effect of solvents and Lewis acids on the stereoselectivity of. reactions of (arylsulfmyl)- and (alkylsulfinyl)benzyl radicals has been examined.

Contrasting Pathways for the Directed Homogeneous Hydrogenation of Vinyl Sulfoxides and Vinyl Sulfones

Rh-complex catalysed directed hydrogenation of (α-hydroxyalkyl)vinyl sulfones follows the same stereochemical course as the corresponding acrylates, via HO-coordination; hydrogenation of the related (α-hydroxyalkyl)vinyl sulfoxides is directed by S-O coor

The Ei Reaction of Substituted threo- and erythro- 1-Phenylethyl Phenyl Sulfoxides

Substituted (RS,SR)-1-phenylethyl phenyl sulfoxides (threo) (XC6H4S(O)CH(CH3)C6H4Y) and some substituted (RR,SS)-sulfoxides (erythro) were prepared and kinetic investigation for the thermal decomposition was carried out at 80.0, 90.0, and 100.0 deg C in dioxane.Hammett plots for threo-XXC6H4S(O)CH(CH3)C6H5 gave positive ρ-values (ρx=0.60-0.64 at three temoeratures), while those for threo- and erythro-C6H5S(O)CH(CH3)C6H4Y showed V-shape lines with bottoms at the m-OCH3 substituent though the effects of the substituents were small.Meanwhile, large kinetic isotope effects for threo- and erythro-C6H5S(O)CH(O)CH(CH3)C6H4Y (Y=H, p-OMe, m-Cl) (kH/kD=4-6) were observed at all temperatures.The activation energies were in the range of 104-121 kJ mol-1 for all sulfoxides, while the activation entropies were relatively large (7-37 JK-1mol-1) and were correlated with Hammett ?-values to give small negative trend.Reactions of all erythro-isomers examined were 2-3 times faster than those of corresponding threo-isomers.From these results, it is suggested that the pyrolysis of 1-arylethyl aryl sulfoxides proceeds via a concerted mechanism in which the transition state is variable from an Ei'1-like to a conjugated one.In the latter transition state, conjugation of the phenyl group bearing the electron-withdrawing substituent with developing ?-bond electron acidifies the β-proton.