211310-44-0

Upstream product

• 34678-67-6 methyl 2,4-dimethylphenyl sulphide 
• 676-85-7 methylsulphinyl chloride 
• 583-70-0 1-bromo-2,4-dimethylbenzene 
• 132260-85-6 4,4'-sulfinylbis(1,3-dimethylbenzene) 
• 2999-74-8 dimethylmagnesium 

Downstream Products

• 211310-46-2 4-(2,4-dimethyl-phenylsulfanyl)-2,3-dihydro-furan 
• 211310-22-4 4-[(2,4-Dimethyl)phenylsulfinyl]-2,3-dihydrofuran 

Relevant academic research and scientific papers

Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols

Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.

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).

Highly enantioselective oxidation of sulfides to sulfoxides by a new oxaziridinium salt

The new oxaziridinium salt 5 (R2 = TBDPS) is an effective reagent for the highly enantioselective oxidation of sulfides to sulfoxides with up to >99% ee and good yields. As such, it represents a new valuable nonmetallic alternative to the existing methods for asymmetric sulfoxidation.