39213-31-5

Upstream product

• 21128-88-1 chloromethyl methyl sulfoxide 
• 108-98-5 thiophenol 
• 56772-75-9 {[(methylsulfanyl)methyl]sulfanyl}benzene 
• 67-68-5 dimethyl sulfoxide 
• 882-33-7 diphenyldisulfane 

Relevant academic research and scientific papers

Metal-free radical thiolations mediated by very weak bases

Aromatic thioethers and analogous heavier chalcogenides were prepared by reaction of arene-diazonium salts with disulfides in the presence of the cheap and weak base NaOAc. The mild and practical reaction conditions (equimolar reagents, DMSO, r.t., 8 h) tolerate various functional groups (e.g. Br, Cl, NO2, CO2R, OH, SCF3, furans). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals.

Dioxygenase-catalysed mono-, di- and tri-oxygenation of dialkyl sulfides and thioacetals: Chemoenzymatic synthesis of enantiopure cis-diol sulfoxides

Toluene dioxygenase (TDO)-catalysed monooxygenation of methylsulfanylmethyl phenyl sulfide 1 and methylsulfanylmethyl 2-pyridyl sulfide 4, using whole cells of Pseudomonas putida UV4, occurred exclusively at the alkyl aryl sulfur centre to yield the alkyl aryl sulfoxides 2 and 5 respectively. These sulfoxides, accompanied by the dialkyl sulfoxides 3 and 6, were also obtained from naphthalene dioxygenase (NDO)-catalysed sulfoxidation of thioacetals 1 and 4 using intact cells of P. putida NCIMB 8859. Enzymatic oxidation of methyl benzyl sulfide 7, 2-phenyl-1,3-dithiane 19, and 2-phenyl-1,3-dithiolane 23, using TDO, gave the corresponding dialkyl sulfoxides 8, 20 and 24 as minor bioproducts. TDO-catalysed dioxygenation of the alkyl benzyl sulfides 7,15 and 17 and the thioacetals 19 and 23, with P. putida UV4, yielded the corresponding enantiopurecis-dihydrodiols 9, 16, 18, 21 and 25 as major metabolites and cis-dihydrodiol sulfoxides 14, 22 and 26 as minor metabolites, resulting from a tandem trioxygenation of substrates 7, 19 and 23 respectively. Chemical oxidation, of the enantiopure cis-dihydrodiol sulfides 9, 16, 18 and 21 with dimethyldioxirane (DMD), gave separable mixtures of the corresponding pairs of cis-dihydrodiol sulfoxide diastereoisomers 14 and 27, 28 and 29, 30 and 31, 22 and 32. While dialkyl sulfoxide bioproducts 3, 6, 20 and 24 were of variable enantiopurity (27-≥98% ee), alkyl aryl monosulfoxides 2 and 5, cis-dihydrodiols 9, 16, 18, 21 and 25 and cis-dihydrodiol sulfoxide bioproducts 14, 22 and 26 were all single enantiomers (≥98% ee). The absolute configurations of the products, obtained from enzyme-catalysed (TDO and NDO) and chemical (DMD) oxidation methods, were determined by stereochemical correlation, circular dichroism, and X-ray crystallographic methods.

Asymmetric Microbial Oxidation of Formaldehyde Dithioacetals

Incubation of formaldehyde dithioacetals with growing cells of Corynebacterium equi IFO 3730 afforded a variety of oxidation products depending on the structure of the substrate.The products with sulfoxide moiety were optically pure and had R configuratio

Sulfoxide derivative and process for its preparation

A novel sulfoxide derivative of the general formula STR1 wherein R1 and R3 are the same or different, and each represents and alkyl group having 1 to 4 carbon atoms, a phenyl group or a halo- or methyl-substituted phenyl group, R2 is a hydrogen atom, a lower alkyl group, benzyl group, or a p-methoxy- or p-bromo-benzyl group, R1 and R2, together, may form an alkylene group containing 3 carbon atoms, and X is an oxygen or sulfur atom, and to a process for its preparation.