188055-10-9

Basic information

• Product Name: 1,1-bis(phenylmethylthio)-1-sulfinylmethane
• Synonyms: 1,1-bis(phenylmethylthio)-1-sulfinylmethane
• CAS NO: 188055-10-9
• Molecular Weight: 306.474
• Mol File: 188055-10-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,1-bis(phenylmethylthio)-1-sulfinylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-bis(phenylmethylthio)-1-sulfinylmethane(188055-10-9)
• EPA Substance Registry System: 1,1-bis(phenylmethylthio)-1-sulfinylmethane(188055-10-9)

Safety Data

• Hazardous Substances Data: 188055-10-9(Hazardous Substances Data)

Upstream product

• 26504-29-0 dibenzyl trithiocarbonate 

Downstream Products

• 10606-38-9 tris(phenylmethylthio)methane 
• 32779-85-4 S-phenylmethyl thioformate 

Relevant articles and documents

Thiophilic addition of organolithiums to trithiocarbonate oxides (sulfines). Synthesis of β-oxoketene dithioacetals, 1,4-dicarbonyl compounds, and allyl sulfoxides

Reaction of trithiocarbonates with meta-chloroperoxybenzoic acid in CH2Cl2 at 0°C affords the corresponding S-oxides. These sulfines are relatively stable comppounds which can be purified by chromatography. They react readily with organolithiums in THF at -78°C in a thiophilic manner to give carbanions which are stabilized by three sulfur groups. Hydrolysis affords trithioorthoester oxides. The thermal behaviour of these hindered products has been investigated and new rearrangenrent processes have been evidenced. The former carbanions are soft nucleophiles: 1,4-addition of these intermediates to α-enones was achieved selectively to lead to β-oxo ketenedithioacetals, which are easily transformed into 4-oxoalkanethioates. This 'Umpolung' route allows the formal use of the (alkylthio)carbonyl anion. A thiophilic addition was also observed with allylsilanes in the presence of n-Bu4NF furnishing allyl sulfoxides.