15848-08-5

Basic information

• Product Name: Methanethione, bis(4-methoxyphenyl)-, S-oxide
• CAS NO: 15848-08-5
• Molecular Formula: C15H14O3S
• Molecular Weight: 274.34
• Mol File: 15848-08-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Methanethione, bis(4-methoxyphenyl)-, S-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Methanethione, bis(4-methoxyphenyl)-, S-oxide(15848-08-5)
• EPA Substance Registry System: Methanethione, bis(4-methoxyphenyl)-, S-oxide(15848-08-5)

Safety Data

• Hazardous Substances Data: 15848-08-5(Hazardous Substances Data)

Upstream product

• 958-80-5 bis(4-methoxyphenyl)thione 
• 106864-88-4 methyl bis(4-methoxyphenyl)methanesulfinate 

Downstream Products

• 50999-10-5 2,2-bis-(4-methoxy-phenyl)-3,5-diphenyl-2,3-dihydro-[1,3,4]thiadiazole 1,1-dioxide 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 958-80-5 bis(4-methoxyphenyl)thione 
• 88534-41-2 9--xanthen 
• 88534-40-1 9-[bis(4-methoxyphenyl)methylidene]-9H-fluorene 
• 50999-06-9 2,2-bis-(4-methoxy-phenyl)-3,5-diphenyl-2,3-dihydro-[1,3,4]thiadiazole 1-oxide 

Relevant articles and documents

A convenient preparation of sulfines (R2C=S=O) from thioketones

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Reaction of Thioketones with Carbonyl Oxides and 3,3-Dimethyl-1,2-dioxirane. Cycloaddition vs. Oxygen Atom Transfer

The ozonolysis of vinyl ethers 1a, b in the presence of adamantane-2-thione 4a and bicyclononan-9-thione 4b gave in each case the corresponding thioozonides 5a-c in moderate yields, whilst ozonolysis of a mixture of vinyl ethers 1a-d and thiobenzophenone derivatives 4f-h gave the corresponding thione S-oxides 8f-h in isolated yields of 10-40percent, together with the benzophenones 7f-h. 3,3-Dimethyl-1,2-dioxirane, generated in situ from the reaction of acetone and 'oxone' (2KHSO5-KHSO4-K2SO4), transferred an oxygen atom to compounds 4a, f, g, i providing the thione S-oxides 8a, f, g, i in 29-97 percent yield.

Elimination Reactions of Alkanesulfinyl Derivatives: Mechanism and Reactivity in Base-Induced Sulfine Formation from Methyl Diarylmethanesulfinates

Upon treatment in methanol at room temperature with methoxide ion methyl diarylmethanesulfinates, ArAr'CHS(O)OCH3 (1), and methyl 9-fluorenesulfinate (2) undergo elimination readily to afford the corresponding sulfines (3 and 4) in quantitative yield.Studies in CD3O-/CD3OD show that, surprisingly, elimination of 1 to give 3 is significantly faster than nucleophilic substitution by methoxide ion at the sulfinyl group (exchange of CH3O by CD3O).Even more unexpected, the kinetic isotope effect for elimination of 2-9-d (kH/kD=6.1) and absence of detectable H/D exchange of the methine proton of 1 in CD3OD prior to sulfine formation extablish that, even though the leaving group is MeO-, the elimination takes place by either an irreversible ElcB or an E2 mechanism, rather than the reversible ElcB mechanism found (ref 4 and 7) for the analogous sulfene-forming elimination of arylmethanesulfonate esters with oxyanion leaving groups of comparable pKa.Reaction of amines with 2 in methanol also gives sulfine 4, and the amine-induced elimination, which has a large Broensted β, also proceeds by either an (ElcB)irrev or an ElcB-like E2 mechanism.Why sulfine-forming eliminations of 1 and 2 favor an (ElcB)irrev or E2 mechanism whereas sulfene-forming eliminations of arylmethanesulfonates with even better leaving groups proceed by an (ElcB)rev mechanism is considered and a possible explanation presented.