5925-63-3

Upstream product

• 37602-94-1 O,O-diethyl S-(2-phenyl)ethyl phosphorodithioate 
• 103-63-9 1-phenyl-2-bromoethane 
• 5188-07-8 sodium thiomethoxide 
• 74-93-1 methylthiol 
• 622-24-2 2-phenylethyl chloride 
• 591-51-5 phenyllithium 
• 24225-08-9 methanesulfonyl cyanide 
• 114050-31-6 3-Phenyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 4410-99-5 2-mercaptophenylethane 
• 74-88-4 methyl iodide 
• 7715-00-6 (2-methanesulfinylvinyl)benzene 
• 637-59-2 1-Bromo-3-phenylpropane 
• 90878-19-6 phenethylmagnesium chloride 
• 42254-80-8 S-methyl thiosulfate O-sodium salt 

Downstream Products

• 6079-56-7 (2-(methylsulfonyl)ethyl)benzene 
• 1075-69-0 (2-phenylethyl)dimethylsulfonium bromide 
• 99103-83-0 1-[4-(2-methylsulfanyl-ethyl)-phenyl]-ethanone 
• 7714-32-1 (2-(methylsulfinyl)ethyl)benzene 
• 100-42-5 styrene 
• 1077-16-3 hexylbenzene 
• 27846-22-6 diphenethyl disulfide 
• 71521-89-6 1-butyl-2-hexylbenzene 
• 933790-72-8 [(p-cymene)RuCl₂(PhC₂H₄SMe)] 
• 28289-44-3 dimethyl-phenethyl sulfonium ; iodide 

Relevant academic research and scientific papers

Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols

Isothiouronium salts are easily accessible and stable compounds. Herein, we report their use as versatile deoxasulfenylating agents enabling a stereoselective, thiol-free protocol for synthesis of thioethers from alcohols. The method is simple, scalable and tolerates a broad range of functional groups otherwise incompatible with other methods. Late-stage modification of several pharmaceuticals provides access to multiple analogues of biologically relevant molecules. Performed experiments give insight into the reaction mechanism.

Chemoenzymatic Deracemization of Chiral Sulfoxides

The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine-type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides.

Ex Situ Formation of Methanethiol: Application in the Gold(I)-Promoted Anti-Markovnikov Hydrothiolation of Olefins

A protocol for the Au-promoted anti-Markovnikov hydrothiolation of olefins using ex situ generated methanethiol is reported. The use of S-methylisothiourea hemisulfate salt as a solid precursor for methanethiol generation ensures a safe and reliable deliverance of a stoichiometric amount of this thiol. The procedure was shown to work for a broad range of olefins providing the corresponding hydrothiolated adduct in good to excellent yields. Mechanistic evaluations suggest that thiyl radicals are generated and that gold acts as an efficient but stable radical initiator.

Pummerer rearrangement using bis(p-nitrophenyl) phosphorazidate as an azidation reagent: A novel synthesis of azidomethyl sulfides

A novel method for the synthesis of azidomethyl sulfides by Pummerer rearrangement using bis(p-nitrophenyl) phosphorazidate (p-NO2DPPA) as an azidation reagent was developed. Various methyl sulfoxides were converted into the corresponding azidomethyl sulfides. Importantly, this reaction enables the preparation of azidomethyl sulfides without the use of toxic or explosive azide sources.

The reaction of grignard reagents with bunte salts: A thiol-free synthesis of sulfides

S-Alkyl, S-aryl, and S-vinyl thiosulfate sodium salts (Bunte salts) react with Grignard reagents to give sulfides in good yields. The S-alkyl Bunte salts are prepared from odorless sodium thiosulfate by an SN2 reaction with alkyl halides. A Cu-

Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase

A bacterial flavin-containing monooxygenase (FMO), fused to phosphite dehydrogenase, has been used to explore its biocatalytic potential. The bifunctional biocatalyst could be expressed in high amounts in Escherichia coli and was able to oxidize indole and indole derivatives into a variety of indigo compounds. The monooxygenase also performs the sulfoxidation of a wide range of prochiral sulfides, showing moderate to good enantioselectivities in forming chiral sulfoxides. The Royal Society of Chemistry 2011.

BISPHOSPHONATE COMPOUNDS AND METHODS

The invention provides, inter alia, novel bisphosphonate compounds and methods of making and using. In embodiments, the invention provides compounds and methods in connection with research and therapeutic applications, e.g., for tumor cell growth inhibiti

Oxidation of benzylic bromides by DMSO in the presence of zinc salts: A new variant of Kornblum's method

Benzyl and 1-phenylethyl bromides are oxidised to benzaldehyde and acetophenone respectively by DMSO in the presence of zinc salts with moderate to high yield. The corresponding alcohol and the thiomethyl ether derivative are formed as by-products. However, 2-phenylethyl bromide affords, under forcing conditions, the corresponding thiomethyl ether and alcohol as major products. This study, besides leading to a new variant of Kornblum oxidation, has given an insight into its mechanism.

Radical Substitution on the Sulfur of Thioester Group. A Substituent Effect on the Reactivity of Thioester to Methyl Radical

Methyl radical reacts with thioesters (-S-CO-) to give methyl sulfide (CH3-S-), substitution products on sulfur.The mechanism is proposed in which the methyl radical attacks the sulfur in an nucleophilic manner in the rate determining step to give a sulfuranyl radical intermediate.

O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide

Reaction of p-toluenesulfonyl cyanide or methanesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]under-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates 9 and 21 is suggested.