22768-79-2

Upstream product

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

Relevant academic research and scientific papers

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.

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.

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.

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.