128092-47-7

Upstream product

• 3085-42-5 bis(4-chlorophenyl)sulfoxide 
• 557-18-6 diethylmagnesium 
• 100461-74-3 (-)-(R)-(p-Chlorophenyl)ethylmethylsulfonium Perchlorate 
• 5120-72-9 p-chlorophenyl ethyl sulfide 

Relevant academic research and scientific papers

Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides

Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β-aminoalkoxide. This worked best when the alkoxide stemmed from a dialkylmagnesium reagent and an equimolar amount of N-methyl-(–)-ephedrine. This second activation mode allowed sulfinylations of what was originally the dialkylzinc reagent with diaryl sulfoxides. This generated alkyl aryl sulfoxides with enantiomeric ratios up to 93:7 in up to 100 % yield.

Symmetric diarylsulfoxides as asymmetric sulfinylating reagents for dialkylmagnesium compounds

At -78 °C, primary dialkylmagnesium compounds reacted with diarylsulfoxides when 1.5 equiv of the dilithium salt of (S)-BINOL was added as a promotor. Alkyl aryl sulfoxides resulted in up to quantitative yield and with up to 97% ee. This demonstrates the feasibility of asymmetric sulfinylations by achiral sulfinylating agents (from the perspective of Alkyl2Mg) as well as the feasibility of asymmetric sulfoxide-magnesium exchanges (from the perspective of Ar2SO).

A new methodology for the oxidation of sulfides with Fe(III) catalysts

A variety of sulfides were converted to the corresponding sulfoxide derivatives with 70% t-BuOOH (water) as the oxidant in the presence of catalytic quantity of Fe2(SO4)3. The method described has a wide range of applicati

Bi2O3 catalyzed asymmetric oxidation of sulfides

Bismuth based catalytic system for the asymmetric oxidation of alkyl and aryl benzyl sulfides using t-BuOOH as the oxidant has been investigated. This method affords sulfoxides with high enantioselectivities (up to 98% ee) and good yields in reasonable time. The over oxidized product namely the sulfone was not observed. The described method has wide range of applications, exhibits chemoselectivity/enantioselectivity, and proceeds under mild and environmentally friendly reaction conditions.

SYNTHESIS AND ABSOLUTE CONFIGURATIONS OF OPTICALLY ACTIVE OXOSULFONIUM SALTS

The optically active arylethylmethyloxosulfonium perchlorates (2a-c) were prepared by the oxidation of the corresponding sulfonium salts (1a-c) with sodium perbenzoate.The absolute configurations of oxosulfonium salts were determined by converting them into aryl ethyl sulfoxides (3a-c).From the relationship of the absolute configurations of ethylmethylphenylsulfonium perchlorate (1a) and ethylmethylphenyloxosulfonium perchlorate (2a), it was found that the oxidation of sulfonium salt (+)-(S)-1a with sodium perbenzoate proceeded with retention of configuration around the sulfur atom to afford oxosulfonium salt (+)-(R)-2a.The circular dichroism (CD) spectra of optically active oxosulfonium perchlorates (2) with (+)-(R) configuration show a positive strong Cotton effect at ca. 230 nm and a positive weak one at ca. 260 nm.Whereas, the CD spectra of optically active oxosulfonium perchlorates (2) with (-)-S configuration show a negative strong Cotton effect at ca. 230 nm and a negative one at ca. 260 nm.