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• 27691-43-6 1-(benzylsulphanyl)-4-Nitrobenzene 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 921765-54-0 3-benzylsulfanylpropionic acid tert-butyl ester 
• 100-53-8 phenylmethanethiol 
• 921765-53-9 3-(phenylmethylsulfinyl)propionic acid tert-butyl ester 
• 636-98-6 p-nitrobenzene iodide 
• 100-44-7 benzyl chloride 
• 1849-36-1 para-nitrobenzenethiol 

Relevant academic research and scientific papers

Titanium-salan-catalyzed asymmetric sulfoxidations with H2O 2: Design of more versatile catalysts

Titanium-salan complexes with 3,3'-diphenyl substituents in the salicylidene rings of the salan ligand are efficient sulfoxidation catalysts, capable of catalyzing the asymmetric oxidation of bulky aryl benzyl sulfides with H2O2 with good to high enantioselectivities. In this paper, substituent effects on titanium-salan-catalyzed enantioselective oxidation of sulfides to sulfoxides have been systematically investigated. Titanium-salan catalysts with halogen substituents at the 5,5'-positions (3,3'-H2dihydrogen substituted) have been found to catalyze the oxidation of both bulky aryl benzyl sulfides and small alkyl phenyl sulfides with good to high enantioselectivities. Kinetic data witness a direct attack of the sulfide to the electrophilic active oxygen species; a consistent reaction mechanism is proposed. Copyright 2013 John Wiley & Sons, Ltd. Titanium-salan complexes with halogen substituents at the 5,5'-positions are versatile catalysts for the oxidation of both bulky aryl benzyl sulfides and small alkyl phenyl sulfides, demonstrating good to high chemoselectivity (up to 92 %) and enantioselectivity (up to 93 % ee). Copyright

Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.

Tetrabutylammonium tribromide impregnated MCM-48 as a heterogeneous catalyst for selective oxidation of sulfides

We report here tetrabutylammonium tribromide supported on MCM-48 as a highly efficient heterogeneous catalyst for the selective oxidation of sulfides, in ethanolic medium using hydrogen peroxide as an oxidant. The aforementioned oxidation reactions were found to proceed rapidly (20 min) and in good yield (85-99%) (17 examples). The oxidation products were characterized by 1H NMR, 13C NMR and elemental analysis. The catalytic properties were analysed by TEM, XRD and BET-surface area measurement. No over-oxidation of the substrates was observed (analysed by GC), and the catalyst was effectively recycled for five consecutive cycles without any significant loss in its catalytic activity.

Sodium hypochlorite-promoted novel synthesis of organic ammonium tribromides and application of phenanthroline hydrotribromide in chemoselective oxidation of organic sulfides by hydrogen peroxide

A novel method of synthesis of organic ammonium tribromides (OATBs) is developed by using an inexpensive and eco-friendly sodium hypochlorite as oxidant for conversion of Br to Br3 . The OATBs thus prepared include both quaternary ammonium tribromides and N-heterocyclic tribromides. A new addition to the family of OATBs is made in the form of phenanthroline hydrotribromide. The efficacy of this new tribromide as catalyst is ascertained in the oxidative transformation of organic sulfides to their corresponding sulfoxides and sulfones by hydrogen peroxide.

TMSCl-promoted selective oxidation of sulfides to sulfoxides with hydrogen peroxide

Selective oxidation of sulfides to sulfoxides is achieved using H 2O2 and TMSCl as the promotor. Aromatic and aliphatic sulfides are oxidized to sulfoxides in excellent yields and in short reaction times. Different functional groups including ketone, alkene, ester, and alcohol are tolerated.

Borax-catalyzed and pH-Controlled selective oxidation of organic sulfides by H2O2: An environmentally clean protocol

The selective oxidation of sulfides to sulfoxides and sulfones was achieved in high yields at: room temperature with borax as a recyclable catalyst and H2O2 as the terminal oxidant by varying the pH of the reaction medium. The borax/H2O2 system can chemoselectively oxidize alkyl and aryl sulfides in the presence of oxidation-prone functional, groups such as C=C, -CN, and -OH.

A combined theoretical and experimental investigation on the enantioselective oxidation of aryl benzyl sulfides in the presence of a chiral titanium catalyst

An experimental investigation of the enantioselective oxidation of aryl benzyl sulfides by tert-butyl hydroperoxide in the presence of a titanium/hydrobenzoin catalyst has shown that these sulfides are ideal substrates for this catalytic system, with negl

Photooxidation of alkyl 4-nitrophenyl sulfides and sulfoxides. Observation of oxidative C-S bond cleavage and rearrangement reactions

Alkyl 4-nitrophenyl sulfides and sulfoxides undergo a self-photoinduced, singlet oxygen oxidation to produce a variety of products, including sulfonates and carbonyl compounds formed by the oxidative cleavage of the C-S bond of the sulfides and sulfoxides. Structural rearrangements are observed in the resulting carbonyl compounds formed in the oxidative cleavage of the C-S bond in the tert-amyl and 2-phenylethyl sulfides. An overall mechanism is proposed which involves the formation of peroxysulfoxides and peroxysulfones which undergo heterolytic C-S bond cleavage to form ion pairs which recombine to form persulfenates or persulfinates which then undergo photo- and/or thermallyinduced homolytic O-O bond cleavage to form alkoxy and sulfinyl or sulfonyl radicals. The alkoxy radicals undergo β-scission, disproportionation, or recombination with the sulfonyl radical to form the observed products. These C-S oxidative cleavage reactions have only been rarely observed in the earlier studies on the singlet oxygen oxidation studies of dialkyl sulfides, and are attributed, in part, to the presence of the 4-nitro group on the aromatic ring which greatly affects the susceptibility of the sulfur atom of the sulfides and sulfoxides toward nucleophilic attack, and on the reactivity of the peroxysulfoxides and peroxysulfones toward heterolytic cleavage of the O-S bond.

Ring Contractions of Thiochroman-4-ones and Thiochromen-4-ones

3-Bromothiochroman-4-one and its S-oxide undergo ring contraction on heating, especially in the presence of sodium acetate, to give mixtures which include thioindigo (9) and the ethanediylidenethioindigo (10).Brominated 2,2-dimethylthiochroman-4-one reacts on silica gel to form thioindigo, thioindirubin, and the bis(benzothieno)pyran (17).Bromination of thiochromanone gives a number of products, including 2,3-dibromothiochromen-4-one S-oxide which, on heating with sodium acetate in acetic acid, is converted efficiently into thioindigo.The mechanism of this reaction is investigated.