26756-22-9

Upstream product

• 7601-90-3 perchloric acid 
• 64-17-5 ethanol 
• 7417-73-4 benzyl t-butyl sulfide 
• 7722-84-1 dihydrogen peroxide 
• 100-53-8 phenylmethanethiol 
• 75-65-0 tert-butyl alcohol 
• 1589-82-8 phenylmagnesium bromide 
• 108-88-3 toluene 
• 31562-40-0 tert-butyl tert-butanethiosulfinate 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 75-66-1 2-methylpropan-2-thiol 
• 49833-28-5 3-(tert-butylsulfinyl)propionic acid ethyl ester 
• 960133-71-5 ethyl ((R_S)-N-tert-butylsulfinyl)iminoacetate 

Downstream Products

• 120446-40-4 (R^*_S,2R^*)-2-(tert-butylsulfinyl)-1,1,2-triphenylethanol 
• 129161-96-2 (3R,4R)-4-(2-Methyl-propane-2-sulfinyl)-3,4-diphenyl-butyric acid methyl ester 
• 120446-43-7 rac-(Ss,1S,2S)-2-(tert-butylsulfinyl)-1,2-diphenylethanol 
• 120446-43-7 rac-(Ss,1R,2S)-2-(tert-butylsulfinyl)-1,2-diphenylethanol 
• 120446-43-7 Erythro-1,2-diphenyl-2-tert-butylsulfinylethanol 
• 120446-43-7 Threo-1,2-diphenyl-2-tert-butylsulfinylethanol 
• 129161-97-3 (2S,3S,4R)-2,3-Dimethyl-4-(2-methyl-propane-2-sulfinyl)-4-phenyl-butyric acid methyl ester 
• 20282-89-7 ((tert-butylsulfonyl)methyl)benzene 
• 35399-78-1 rac-(Ss,1S)-tert-butyl 1-phenylethyl sulfoxide 
• 40723-04-4 phenylmethanesulfinic acid phenylamide 
• 96936-34-4 S-benzyl N-benzylthiocarbamate 

Relevant academic research and scientific papers

Stereochemistry of Oxygenation of Organic Sulphides with Pig Liver Microsomal FAD-containing Mono-oxygenase: Comparison with Cytochrome P-450PB Oxidations

The enantiotopic differentiating ability of pig liver microsomal FAD-containing mono-oxygenase (EC 1.14.13.8) in the oxygenation of nine unsymmetrical sulphides has been investigated.By this enzymatic oxygenation, the sulphides are converted into the corr

Thermolysis-Induced Two- or Multicomponent Tandem Reactions Involving Isocyanides and Sulfenic-Acid-Generating Sulfoxides: Access to Diverse Sulfur-Containing Functional Scaffolds

Direct reaction of isocyanides with some sulfenic-acid-generating sulfoxides led to the effective formation of the corresponding thiocarbamic acid S-esters in good to high yields. A multicomponent reaction involving isocyanide, sulfoxide, and a suitable nucleophile has also been developed, providing ready access to a diverse range of sulfur-containing compounds, including isothioureas, carbonimidothioic acid esters, and carboximidothioic acid esters.

Tert-Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts

The present report describes an efficient and clean generation of sulfenate salts (R1SO-) by pyrolysis of readily available tert-butyl sulfoxides to give sulfenic acids (R1SOH) and traceless isobutene, followed by hydrogen abstraction with a weak inorganic base (K3PO4). The relevance of this process was exemplified through an in situ palladium-catalyzed cross-coupling reaction with aryl halides/triflates leading to aryl sulfoxides. The operationally simple C-S bond-forming protocol developed uses Pd(dba)2 as catalyst and Xantphos as ligand in toluene or a toluene/H2O mixture. Further extensions include the use of di-tert-butyl sulfoxide as an equivalent for sulfur monoxide dianion (SO2-) and the development of diastereoselective versions in the [2.2]paracyclophane and biaryl series.

Diastereoconvergent synthesis of trans -5-hydroxy-6-substituted-2- piperidinones by addition-cyclization-deprotection process

A diastereoselective one-pot approach to access trans-5-hydroxy-6- substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by α-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.

Enantioselective synthesis of benzyl tert-butyl sulfoxides

Enantiomerically pure benzyl sulfoxides are effective tools for the formation of new C-C bonds with control of configuration at new stereogenic centres. The reaction of enantioenriched tert-butyl tert-butanethiosulfinate with benzyllithium derivatives, ob

trans-(±)-2-tert-butyl-3-phenyloxaziridine: A unique reagent for the oxidation of thiolates into sulfenates

(Chemical Equation Presented) Aliphatic thiolates were efficiently converted into the corresponding sulfenates by smooth oxidation with trans-(±)-2-tert-butyl-3-phenyloxaziridine at room temperature (five examples). Subsequent electrophilic quench with benzyl bromide led to sulfoxides (S-alkylation) in good to moderate yields. Application of the protocol to an aromatic substrate was also successful. This work represents the first valuable example of the use of this poorly active oxidizing agent in synthetic organic chemistry without the need for activating conditions.

Reaction of singlet oxygen with some benzylic sulfides

Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, α-methylbenzyl, and cumyl sulfides. Their contributions depend on the steric hindering around the sulfur atom. In protic solvents, the sulfoxide is the main product via a hydrogen-bonded persulfoxide. In apolar solvents, intramolecular α-H abstraction leads to oxidative C-S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.

Asymmetric synthesis of aryl benzyl sulfoxides by vanadium-catalysed oxidation: A combination of enantioselective sulfide oxidation and kinetic resolution in sulfoxide oxidation

Enantioselective vanadium-catalysed oxidation of aryl benzyl sulfides using Bolm's procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90% ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Remarkably mild and simple preparation of sulfenate anions from β-sulfinylesters: A new route to enantioenriched sulfoxides

(Chemical Equation Presented) A general, efficient, and experimentally simple method for the generation of sulfenate salts has been developed using β-sulfmylesters as substrates. The process is based on a retro-Michael reaction, initiated by deprotonation at low temperature. Upon treatment with alkyl halides, the liberated sulfenates are subsequently converted into sulfoxides in good to excellent yield. Extension of the methodology to an unprecedented access to nonracemic sulfoxides by introduction of an enantiopure ligand, (-)-sparteine, is also described.

A novel method for the stereoselective synthesis of tetralins and indanes

Heavily-substituted 1-aryltetralins and 1-arylindanes were prepared in a highly stereoselective manner using a two-step sequence. Addition of t-butyl benzyl sulfoxides to unsaturated carbonyl compounds gave conjugate adducts with high diastereoselectivity