963-16-6

Usage

Uses

Used in Pharmaceutical Synthesis:
TRANS-1,2-BIS(PHENYLSULFONYL)ETHYLENE is used as a key intermediate in the total synthesis of (+)-7-deoxypancratistatin, a natural product with potential anticancer properties. Its unique structure allows for efficient construction of the complex molecule.
Used in Natural Product Synthesis:
In the field of natural product synthesis, TRANS-1,2-BIS(PHENYLSULFONYL)ETHYLENE is useful for the synthesis of dysiherbaine and neodysiherbaine A, which are bioactive alkaloids with potential applications in medicine.
Used in Catalytic Enantioselective Reactions:
TRANS-1,2-BIS(PHENYLSULFONYL)ETHYLENE has been employed in chiral BINAP-AuTFAand chiral BINAP-AgTFA (TFA = trifluoroacetate anion) -promoted catalytic enantioselective 1,3-dipolar cycloadditions of iminoglycinates. This application highlights its utility in the development of enantioselective synthetic methods, which are crucial for the production of chiral molecules with specific biological activities.

InChI:InChI=1S/C14H12O4S2/c15-19(16,13-7-3-1-4-8-13)11-12-20(17,18)14-9-5-2-6-10-14/h1-12H/b12-11+

Upstream product

• 18893-62-4 cis-1,2-bis-phenylsulfanyl-ethylene 
• 963-15-5 (Z)-1,2-bis(phenylsulfonyl)ethene 
• 20408-25-7 trans-β-Bromovinyl phenyl sulfone 
• 13411-42-2 2-(trimethylsilyl)-1,3-dithiane 
• 38238-75-4 (E)-2-chloroethenyl phenyl sulfone 
• 873-55-2 sodium benzenesulfonate 
• 105-53-3 diethyl malonate 
• 26620-11-1 (E)-2-chlorovinylthiobenzene 
• 98-09-9 benzenesulfonyl chloride 
• 3123-10-2 Phenyl-β,β-dichlorethylsulfon 
• 39082-53-6 1,1-bis(phenylsulfonyl)ethylene 
• 6262-45-9 1,2-dichloro-3,3-difluorocyclopropene 
• 618-41-7 Benzenesulfinic acid 
• 18893-63-5 (E)-1,2-bis(phenylsulfanyl)ethylene 

Downstream Products

• 87057-40-7 (+/-)-trans-2,3-bis(phenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene 
• 115307-29-4 1-<(E)-2-(phenylsulphonyl)ethenyl>-5-(iodomethyl)-2-pyrrolidinone 
• 93914-95-5 C₂₁H₂₂O₆S₂ 
• 87057-41-8 5-exo,6-endo-bis(phenylsulfonyl)bicyclo<2.2.2>non-7-ene 
• 87057-42-9 (1R,6S,9R,10R)-9,10-Bis-benzenesulfonyl-tricyclo[4.2.2.0^2,5]deca-3,7-diene 
• 87057-42-9 5-exo,6-endo-bis(phenylsulfonyl)tricyclo<4.2.2.0^2,5>deca-3,9-diene 
• 88132-63-2 racemic 1,2-bis(phenylsulfonyl)-9,10-ethanoanthracene 
• 93914-97-7 (1R,4S,5S,6S)-6-Benzenesulfonyl-5-hydroxy-bicyclo[2.2.1]heptan-2-one 
• 93914-92-2 (1S,4R,5S,6S)-5,6-Bis-benzenesulfonyl-bicyclo[2.2.1]heptan-2-one 
• 93914-92-2 (1R,4S,5S,6S)-5,6-Bis-benzenesulfonyl-bicyclo[2.2.1]heptan-2-one 
• 105632-36-8 (2R*,3S*)-2-<(benzyloxy)-methyl>-3-<<<(E)-2-(phenylsulfonyl)ethenyl>oxy>methyl>-oxirane 
• 128600-98-6 C₂₃H₂₂O₄S₂ 
• 93914-94-4 (1S,4R,5S,6S)-5,6-Bis-benzenesulfonyl-bicyclo[2.2.2]octan-2-one 
• 117985-34-9 trans-2,3-dihydro-9-methyl-1,2-bis(phenylsulfonyl)-1H-pyrrolo<1,2-a>indole 

Relevant academic research and scientific papers

Organocatalytic addition on l,2-bis(sulfone)vinylenes leading to an unprecedented rearrangement

A study was conducted to demonstrate the use of 1,2-bis(sulfone)vinylenes in enamine catalysis. It was revealed that these sulfones led to a new rearrangement arising from a sulfone shift to the adjacent carbon atom. Investigations also revealed that the use of cheaper (Z)-1,2-bis(sulfone) vinylene lead to full conversion after a short reaction time in dioxane, using H2O as co-catalyst to accelerate the reaction. A careful NMR investigation indicated that the new product was gem-disulfone, which was supported by authentic sample.

A novel and simple route for the synthesis of 3,4-disubstituted pyrroles

A new class of 3,4-disubstituted pyrroles has been prepared by the reaction of 1-aroyl-2-arylsulfonylethenes and 1,2-diarylsulfonylethenes with tosyl methyl isocyanide.

Organic semiconductor material and organic electronic device

An organic semiconductor material comprising a compound which has a generalized porphyrin skeleton and which has a molecular structure such that the distance from the generalized porphyrin ring plane to the center of each atom forming the generalized porp

A novel route for the synthesis of unsaturated oxo sulfones and bissulfones

The reaction between vinyl chloride and aroyl/arylsulfonyl chloride under Friedel-Craft's reaction conditions was the basis for the synthesis of unsaturated oxo sulfones and bissulfones.

Diazo transfer reaction of 2-(trimethylsilyl)-1,3-dithiane with tosyl azide, carbenic reactivity of transient 2-diazo-1,3-dithiane

A novel diazo transfer reaction of 2-lithiated 2-(trimethylsilyl)1,3-dithiane with tosyl azide in a 1:20 HMPA-THF mixture furnishes 2-diazo-1,3-dithiane 2, which decomposes at about 0°C to;give in fairly high yield bis(1,3-dithianylidene) 5 through formal

(Z)- and (E)-1,2-Bis(phenylsulfonyl)ethylenes as Synthetic Equivalents to Acetylene as Dienophile

A new method for introducing an ethylenic bridge via a cycloaddition reaction has been developed.It makes use of either (Z)- or (E)-1,2-bis(phenylsulfonyl)ethylene (5 or 6) as synthetic equivalents of acetylene.The high activation due to the two sulfonyl groups promotes cycloaddition even to very unreactive dienes.The removal of the two sulfonyl groups for the required formation of the carbon-carbon double bond is promoted by reduction with metal amalgams in high yields.These properties, associated with the stability of the reagents and the ease of performance of the reactions, make this method a very useful synthetic tool for the preparation of polycyclic dienes and a valid alternative to the commonly available reagents that largely depend upon oxidative methods.

REACTIONS OF 1,2-DICHLORO-3,3-DIFLUOROCYCLOPROPENE WITH POTASSIUM THIOCYANATE AND SODIUM ARYLSULFINATES. SYNTHESIS OF 1,2-DITHIOCYANO-3,3-DIFLUOROCYCLOPROPENE

The reaction of potassium thiocyanate with 1,2-dichloro-3,3-difluorocyclopropene in DMF leads to the formation of 1,2-dithiocyano-3,3-difluorocyclopropene.In contrast, the reaction of sodium arysulfinates with 1,2-dichloro-3,3-difluorocyclopropene or tetrachlorocyclopropene gave (E)-1,2-bis(arylsulfonyl)ethene as the only prouct.