80283-61-0

Upstream product

• 62384-73-0 (E)-1,4-bis(phenylsulfonyl)-2-butene 
• 194851-85-9 ethyl (E)-1-(phenylsulfonyl)-1-buten-3-yl carbonate 
• 115373-63-2 cis-1,4-bis(phenylthio)-1-butene 
• 100-58-3 phenylmagnesium bromide 
• 2204-64-0 4-chloro-1-(benzenesulfonyl)-2-butene 
• 82480-43-1 C₁₆H₁₆O₄S₂ 
• 344739-60-2 C₁₆H₁₆O₄S₂ 
• 930-69-8 sodium thiophenolate 
• 10575-06-1 but-1-yn-4-yl phenyl sulfide 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 873-55-2 sodium benzenesulfonate 
• 3112-85-4 methylphenylsulfonate 
• 19169-90-5 bromomethylphenylsulfone 
• 106-95-6 allyl bromide 

Downstream Products

• 82480-44-2 (2,4-Diethoxy-butane-1-sulfonyl)-benzene 
• 410523-62-5 2-[5-((E)-2-benzenesulfonylvinyl)-4,5-dihydroisoxazol-3yl]pyridine 
• 410523-61-4 5-((E)-2-benzenesulfonylvinyl)-3-phenyl-4,5-dihydroisoxazole 
• 90704-16-8 1,4'-Bis-benzenesulfonyl-2'-ethyl-5-methyl-1H,1'H-[3,3']bipyrrolyl 
• 90704-15-7 1,4'-Bis-benzenesulfonyl-5-methyl-1H,1'H-[3,3']bipyrrolyl 
• 90704-18-0 1-(1'-Benzenesulfonyl-5'-methyl-1H,1'H-[3,3']bipyrrolyl-2-yl)-2-methanesulfinyl-ethanone 
• 90704-17-9 ethyl 5-methyl-1-(phenylsulfonyl)-3,3'-bipyrrole-2'-carboxylate 
• 107914-16-9 1-Benzenesulfonyl-4-((E)-2-benzenesulfonyl-vinyl)-2-methyl-1H-pyrrole 
• 410523-69-2 5-(2-benzenesulfonyl-ethyl)-3-phenyl-isoxazole 

Relevant academic research and scientific papers

A convenient synthesis of (E)-conjugated polyene sulfonyl derivatives with excellent stereospecificity

A highly selective synthesis of conjugated polyene sulfonyl derivatives is described via the elimination of disulfonyl chloride with readily accessible raw material dihaloalkane. The protocol offers a convenient way to form sulfonamides, sulfonates and even sulfones. Furthermore, this method was manipulated under mild condition with simple operation in high yield to afford only trans products.

Diazo reactions with unsaturated compounds: XI. Reactions of benzene-, p-methylbenzene-, and p-methoxybenzenesulfonyl-1,3-butadienes with arenediazonium chlorides and 1-aryl-3,3-dimethyl-1-triazenes

1-(p-Methylbenzene)-and 1-(p-methoxybenzenesulfonyl)-1,3-butadienes in aqueous acetone in the presence of copper(I) or copper(II) chlorides react with arenediazonium chlorides and 1-aryl-3,3-dimethyl-1-triazenes to form 1-(p-methylbenzene)-and 1-(p-methox

Polystyrene-Supported α-Seleno Carbanions: Efficient Reagents for Highly Stereocontrolled Syntheses of Vinylphosphonates and Vinylsulfones

Polystyrene-supported selenomethyl-phosphonate and polystyrene-supported selenomethyl-sulfonates have been prepared. These novel reagents were treated with LDA (or n-BuLi) to produce polystyrene-supported α-seleno carbanions, which reacted with alkyl halides, followed by stereospecific selenoxide syn-elimination to give E-vinylphosphonates and E-vinylsulfones respectively. And also these novel polymer reagents can be regenerated and reused.

Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides

Unlike traditionally used acyclic 1,2-disubstituted alkenes, the reaction of α,β-unsaturated phenyl sulfones with aryl iodides under Heck reaction conditions (Pd(OAc)2 as catalyst, Ag2-CO3 as base in DMF at 120°C) takes place mainly by a cascade process, involving one unit of the alkene and three units of the aryl iodide, to afford a substituted 9-phenylsulfonyl-9,10-dihydrophenanthrene, The dominant formation of this 3:1 coupling product, instead of the Heck trisubstituted olefin, shows that aromatic C-H activation processes can compete with the usually fast syn β-hydrogen elimination step in the Heck arylation of an acyclic olefin. The structural scope of this palladium-catalyzed cascade arylation of α,β-unsaturated sulfones has proved to be wide with regard to substitution at the β-position (alkyl, aryl, or alkenyl substitution), substitution at the sulfone unit (alkyl or phenyl sulfones), and configuration at the C=C bond (trans or cis). Moreover, although less favored than in the case of the arylation of α,β-unsaturated sulfones, similarly substituted 9,10-dihydrophenanthrenes have also been obtained in the case of α,β-unsaturated phosphine oxides and α,β-unsaturated phosphonate esters. A Pd0-pdII-pdIV mechanistic pathway involving the successive formation of highly electrophilic σ-alkylpalladium intermediates and palladacycles is proposed for this multi-component arylation.

1,3-Dipolar cycloaddition of nitrile oxides to 1-phenylsulfonyl-1,3-butadienes: Synthesis of 3-(4,5-dihydroisoxazol-5-yl)pyrroles

Novel heterocyclic compounds containing the 3-(4,5-dihydroisoxazol-5-yl)pyrrole ring system were synthesized in good yields (66-78%) by regioselective 1,3-dipolar cycloaddition of nitrile oxides to 1-phenylsulfonyl-1,3-dienes followed by Barton-Zard pyrrole annulation.

One-step palladium-catalyzed synthesis of substituted dihydrofurans from the carbonate derivatives of γ-hydroxy-α,β-unsaturated sulfones

The palladium-catalyzed nucleophilic allylic substitution of the carbonate derivatives of γ-hydroxyα,β-unsaturated sulfones (2) with soft carbon nucleophiles such as malonates, β-keto esters, 1,3-diketones, and α- sulfonyl ketones took place cleanly and with full regiocontrol (γ- substitution). Typical optimized conditions are Pd2(dba)3 (5 mol %), dppe (20 mol %), molecular sieves, in toluene-THF at 100 °C. Unexpectedly, when β-keto esters, 1,3-diketones, and α-sulfonyl ketones were used as nucleophiles a cascade process occurred, via initial γ-regioselective allylic substitution and further intramolecular conjugate addition of the enol moiety to the α,β-unsaturated sulfone, to give 2,3,4,5- tetrasubstituted dihydrofurans (13-25) in moderate to good yields. Moreover, the cyclization step is highly stereoselective giving predominantly or exclusively the 4,5-dihydrofuran of trans configuration. From readily available enantiopure (S)-2, this one-step procedure of synthesis of substituted dihydrofurans has been applied to the synthesis of enantiomerically pure tetrasubstituted tetrahydrofurans.

Conjugate addition of allylic and prop-2-ynylic alcohols to 3-halogeno-1-phenylsulfonylprop-1-enes; synthesis and radical induced cyclization of 2-alkenyloxy-3-halogenopropylphenyl sulfones

Allylic and prop-2-ynylic alcohols add in a conjugate fashion to 3-halogeno-1-phenylsulfonylprop-1-enes in the presence of KF-basic alumina and the resulting halogenoallyl sulfones can be efficiently cyclized using tributyltin hydride under various conditions.

Preparation of Some Novel Butyl, Butenyl, Butadienyl and Bytynyl Sulfone Electrophiles for Use in Enolate Trapping Studies

The preparation of some novel four-carbon electrophiles and electrophile intermediates is described.Thus, the chlorobutenyl sulfone (5), the iodobutynyl sulfone (6) and the hitherto unreported chlorobutynyl sulfone (4) were prepared.The novel intermediates, containing a chelating imidazolyl functionality, the N-methylimidazolyl sulfides (13)-(15) were also prepared.However, they polymerized rapidly, thus preventing further synthetic manipulations.The preparation of the α-(trimethylsilyl)butadienyl sulfones (17) and (18) is described and the mode of formation of the intermediate α-trimethylsilyl sulfides (21) and (22) from the trimethylsilylbutenyl sulfide (27) is discussed.

FACILE ROUTE TO 1-PHOSPHORYL- AND 1-SULFONYL-1,3-DIENES VIA PALLADIUM-CATALYZED ELIMINATION OF ALLYLIC ACETATES

The palladium(II)-catalyzed chloroacetoxylation of 1,3-dienes is employed to prepare 1-chloro-4-acetoxy-2-alkenes which are then transformed into 1-phosphoryl- or 1-sulfonyl-4-acetoxy-2-alkenes respectively.Elimination of acetate is promoted by palladium(

The Contribution of Ring Strain to Nucleofugality: the First Measurement

Comparison of eliminative ring fission in a cyclopropane and elimination in an acyclic analogue allows determination of acceleration of elimination by ring strain; a factor of at least 1011.7 has been found, the largest for any heterocyclic reaction.