21884-52-6

Basic information

• Product Name: (R,S)-bis-(p-tolylsulfinyl)ethane
• CAS NO: 21884-52-6
• Molecular Weight: 306.45
• Mol File: 21884-52-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R,S)-bis-(p-tolylsulfinyl)ethane(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-bis-(p-tolylsulfinyl)ethane(21884-52-6)
• EPA Substance Registry System: (R,S)-bis-(p-tolylsulfinyl)ethane(21884-52-6)

Safety Data

• Hazardous Substances Data: 21884-52-6(Hazardous Substances Data)

Upstream product

• 10349-05-0 1,2-bis(p-tolylsulfinyl)ethane 
• 106-45-6 para-thiocresol 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 399518-78-6 di(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (S,S)-ethane-1,2-bis-sulfinate 
• 3238-95-7 1,2-bis(p-tolylthio)ethane 

Relevant articles and documents

Vanadium catalyzed enantioselective oxidation of sulfides: Easy transformation of bis(arylthio)alkanes into C2 symmetric chiral sulfoxides

A facile and selective method for the title transformation is described. The two-phase oxidation of bis-sulfides with hydrogen peroxide catalyzed by vanadium complex of chiral Schiff base leads to the corresponding chiral mono- and bis-sulfoxides. In the

Dynamic kinetic transformation of sulfinyl chlorides: Synthesis of enantiomerically pure C2-symmetric bis-sulfoxides

Two modular and highly convergent approaches for the synthesis of both isomers of a large number of optically pure C2-symmetric bis-sulfoxides have been developed, and their scope and limitations have been assessed. The first one uses as intermediate diastereomerically pure C2-symmetric bis-sulfinate esters 6(Ss,Ss) and 6(Rs,Rs), obtained by dynamic kinetic resolution of ethane-1,2-bis-sulfinyl chloride 5. A single inducer of chirality, the glucose-derived DAG (diacetone-D-glucose) 1 is used for the enantioselective synthesis of both diastereomerically pure C2-symmetric bis-sulfinate esters, thanks to the opposite stereodirecting effect of pyridine and iPr2NEt used to catalyze the reaction. The second approach is based on the copper-catalyzed oxidative coupling of optically pure lithiomethyl sulfoxides. Both isomers of a large number of methyl sulfoxides can be obtained in a convergent manner using (Rs)- and (Ss)-DAG methanesulfinate esters 8Rs and 8Ss. Methanesulfinates 8Rs and 8Ss are also obtained in an enantioselective way by a dynamic kinetic resolution of methane sulfinyl chloride 24. The final bis-sulfoxides are obtained with enhanced enantioselectivities compared to the corresponding monomers, as a result of the Horeau effect which is operating in both approaches. A model based on the formation of pentacoordinated sulfur intermediate is proposed. This model can explain the dynamic kinetic resolution observed via Berry pseudorotations, without the commonly accepted in situ racemization of the starting material. The usefulness of the approaches is demonstrated by the preparation of complexes of Pd(II) and Ru(II) bearing bidentated chiral sulfoxides as ligands.