28403-86-3

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 66080-24-8 pinacol 1-(phenylthio)ethane-1-boronate 
• 61173-85-1 2,2-bis(phenylthio)-1-phenylpropan-1-ol 
• 30294-12-3 2,4,6-Trinitro-benzenesulfonic acid (E)-1-phenyl-2-phenylsulfanyl-propenyl ester 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 931-59-9 benzenesulfenyl chloride 
• 673-32-5 1-Phenylprop-1-yne 
• 64168-52-1 4'-nitrobenzenesulfenanilide 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 7205-91-6 phenylthiomethyl chloride 
• 123630-54-6 (E)-1-acetoxy-1-phenyl-2-phenylthiopropene 
• 6084-17-9 2-chloro-1-phenylpropan-1-one 
• 108-98-5 thiophenol 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 

Downstream Products

• 101704-34-1 2-Phenyl-3-phenylsulfanyl-butan-2-ol 
• 79749-83-0 3-methyl-4-oxo-4-phenyl-3-(phenylthio)butanoic acid 
• 27839-91-4 1-phenyl-2-(phenylsulfonyl)-propan-1-one 
• 69358-42-5 1-phenyl-2-(phenylsulfinyl)-1-propanone 
• 90500-92-8 1-phenyl-2-phenylthio-1-propenyl diphenyl phosphate 
• 82416-11-3 2,2-bis(phenylthio)propiophenone 
• 38868-78-9 2,2-dimethoxy-1-phenylpropan-1-one 
• 769-59-5 3-phenyl-butan-2-one 
• 40206-44-8 2-phenyl-3-phenylthio-2-butene 
• 117841-14-2 2-chloro-2-(phenylsulfonyl)-1-phenylpropanone 
• 117841-12-0 erythro-2-chloro-1-phenyl-2-phenylsulfonylpropanol 
• 117841-12-0 threo-2-chloro-1-phenyl-2-phenylsulfonylpropanol 
• 882-33-7 diphenyldisulfane 
• 101704-39-6 C₁₆H₁₆S 

Relevant academic research and scientific papers

Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.

Copper-Catalyzed Synthesis of gem-Bisarylthio Enamines under Redox-Neutral Conditions

An efficient approach for the construction of gem-bisarylthio enamines via coupling of oxime acetates with diaryl disulfides is developed. This process involved copper-catalyzed N?O/S?S bond cleavages and formation of two new C?S bonds. A broad range of s

Tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols

An efficient and highly atom-economical tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols has been developed. This one-step procedure has a wide substrate scope with respect to substituents at

Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes

A catalytic, enantioselective, Lewis base-catalyzed α-sulfenylation of silyl enol ethers has been developed. To avoid acidic hydrolysis of the silyl enol ether substrates, a sulfenylating agent that did not require additional Br?nsted acid activation, namely N-phenylthiosaccharin, was developed. Three classes of Lewis bases - tertiary amines, sulfides, and selenophosphoramides - were identified as active catalysts for the α-sulfenylation reaction. Among a wide variety of chiral Lewis bases in all three classes, only chiral selenophosphoramides afforded α-phenylthio ketones in generally high yield and with good enantioselectivity. The selectivity of the reaction does not depend on the size of the silyl group but is highly sensitive to the double bond geometry and the bulk of the substituents on the double bond. The most selective substrates are those containing a geminal bulky substituent on the enoxysilane. Computational analysis revealed that the enantioselectivity arises from an intriguing interplay among sterically guided approach, distortion energy, and orbital interactions.

Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using α-(phenylthio)isobutyrophenone

In the presence of catalytic amounts of RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-benzothiazoles, 1,3-benzoxazoles, and benzothiophene reacted with α-(phenylthio) isobutyrophenone giving 2-phenylthio derivatives. Reactive monocyclic heteroaromatics, 1-methyl-1,2,3,4-tetrazole and 2-cyanothiophene were also converted into the 5-phenylthio derivatives. The use of an appropriate phenylthio transfer reagent is crucial for the efficient catalyzed conversion of heteroaromatic C-H bonds into C-S bonds.

Rhodium-catalyzed organothio exchange reaction of α-organothioketones with disulfides

RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.

The effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates

Highly Z-selective olefination of acyclic α-thio and α-selenoketones with ynolates has been achieved, and the theoretical calculations of the transition states in the ring-opening of the intermediates, the β-lactone enolates, revealed that the torquoselectivity was controlled by the secondary orbital interactions between the σ orbital of the C-S bond or a lone pair orbital on the S and σ* orbitals of the breaking C-O bond, and the σ orbital of the breaking C-O bond or a lone pair orbital on the O on the ring and the σ* orbitals of the C-S bond. The synthetic applications of the resulting olefins are also shown.

Structure-activity relationship of antileishmanials neolignan analogues

Twenty-two synthetic analogues of neolignans comprising β-ketoethers and β-ketosulfides were obtained from condensation reactions among β-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against

Regiospecific synthesis of α-diones, α,α-dialkoxyketones and α-alkoxy-α-sulfenylated ketones

A convenient synthesis of α-diones and their monoprotected acetals, i.e. α-ketoacetals, was developed by mercury induced solvolysis of regiospecifically formed α-chloro-α-(alkylthio)ketones. Analogously, α-alkoxy-α-sulfenylated ketones were formed when reacting α-chloro-α-sulfenylated ketones with an alkaline alcoholic medium, α-Alkoxy-α-sulfenylated ketones themselves could be transformed into α-diones or ?-ketoacetals, which in turn were hydrolyzed under anhydrous conditions into the corresponding α-diones. (C) 2000 Elsevier Science Ltd.

A facile phase-transfer catalysed synthesis of some β-ketosulphones

Reaction of phenacyl chloride with sodium benzenesulphinate in refluxing alcohol for 10-12 hr results in the formation of phenylsulphonylacetophenone in about 50% yield. However, use of triethyibenzylammonium chloride as phase- transfer catalyst in acetonitrile medium at room temp. gives the product in over 90% yield in 30 min's, reaction time. Optimum conditions are described for the above reaction by changing the solvent, catalyst, temperature and the type of phase-transfer catalysis itself. Using the optimum conditions, several β-ketosulphones have been synthesised in a facile manner by changing the α-haloketone and sulphinate salts.