87231-07-0

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 67-68-5 dimethyl sulfoxide 
• 542-81-4 sulfure de methyle et de 2-chloroethyle 
• 100-44-7 benzyl chloride 
• 14198-13-1 (3-(methylsulfinyl)propyl)benzene 
• 591-50-4 iodobenzene 
• 2432-51-1 ethylthioacetic acid methyl ester 
• 4119-41-9 1-iodo-3-phenylpropan 
• 13532-18-8 methyl 3-(methylthio)propionate 
• 300-57-2 allylbenzene 
• 74-93-1 methylthiol 

Downstream Products

• 14198-13-1 (3-(methylsulfinyl)propyl)benzene 
• 17334-45-1 (3-(methylsulfonyl)propyl)benzene 
• 408533-53-9 Chlormethyl-<γ-phenyl-propyl>-sulfid 
• 1448592-05-9 C₁₀H₁₆S 
• 1240557-70-3 Br^(1-)*C₁₂H₁₇O₂S⁽¹⁺⁾ 
• 960593-10-6 C₁₂H₂₀O₆P₂S 

Relevant academic research and scientific papers

Copper-catalyzed thiocarbonylation and thiolation of alkyl iodides

In the present study, an efficient Cu-catalyzed transthiolation of alkyl iodides is developed. Notably, in the presence of CO, thioesters could also be obtained with copper and cobalt as the co-catalyst. This transformation displayed good functional group

Copper-Catalyzed direct thioetherification of Alkyl Halides with S-Alkyl Butanethioate as Thiol transfer reagent

A new and convenient copper-catalyzed synthesis of alkyl sulfides has been accomplished using S-alkyl butanethioate as a thiol source. This catalytic protocol displayed a good functional groups tolerance and high efficiency. Both secondary and primary alkyl iodides can be used in this procedure. In addition, this method features operational simplicity and a wide substrate range, providing a complementary method for alkyl sulfide synthesis without requiring toxic thiols and noble metals.

Ex Situ Formation of Methanethiol: Application in the Gold(I)-Promoted Anti-Markovnikov Hydrothiolation of Olefins

A protocol for the Au-promoted anti-Markovnikov hydrothiolation of olefins using ex situ generated methanethiol is reported. The use of S-methylisothiourea hemisulfate salt as a solid precursor for methanethiol generation ensures a safe and reliable deliverance of a stoichiometric amount of this thiol. The procedure was shown to work for a broad range of olefins providing the corresponding hydrothiolated adduct in good to excellent yields. Mechanistic evaluations suggest that thiyl radicals are generated and that gold acts as an efficient but stable radical initiator.

Pummerer rearrangement using bis(p-nitrophenyl) phosphorazidate as an azidation reagent: A novel synthesis of azidomethyl sulfides

A novel method for the synthesis of azidomethyl sulfides by Pummerer rearrangement using bis(p-nitrophenyl) phosphorazidate (p-NO2DPPA) as an azidation reagent was developed. Various methyl sulfoxides were converted into the corresponding azidomethyl sulfides. Importantly, this reaction enables the preparation of azidomethyl sulfides without the use of toxic or explosive azide sources.

Regiochemistry and reactivity in the chlorination of sulfides

Huheey's original method for the calculation of substituent electronegativities is modified so that isomeric groups have different electronegativities.The modified form of Huheey's method is then employed to show that our previously published method for anticipating regiochemistry in asymmetric sulfide chlorination, i.e., ΔXP calculations for the α and α' substituents in the sulfide substrates, is successful in all fifty known cases.A new reactivity function (RP) is defined, for the sulfenium ion intermediates, which permits one to anticipate when substrates become inert to chlorine in exhaustive chlorinations conducted in aprotic media.