80283-59-6

Basic information

• Product Name: Benzene, [[(1E)-3-methyl-1,3-butadienyl]sulfonyl]-
• CAS NO: 80283-59-6
• Molecular Formula: C11H12O2S
• Molecular Weight: 208.281
• Mol File: 80283-59-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzene, [[(1E)-3-methyl-1,3-butadienyl]sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [[(1E)-3-methyl-1,3-butadienyl]sulfonyl]-(80283-59-6)
• EPA Substance Registry System: Benzene, [[(1E)-3-methyl-1,3-butadienyl]sulfonyl]-(80283-59-6)

Safety Data

• Hazardous Substances Data: 80283-59-6(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 18955-77-6 γ,γ-dimethylallenyl phenyl sulfone 
• 37605-43-9 3-methyl-1-(phenylsulfinyl)buta-1,2-diene 
• 51892-55-8 cis 1,4-dichloro-2-methyl-2-butene 
• 873-55-2 sodium benzenesulfonate 
• 81582-87-8 (3-methylbut-3-enylsulfonyl)benzene 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 3112-85-4 methylphenylsulfonate 
• 410523-60-3 1-benzenesulfonyl-3-methyl-but-3-en-2-ol 
• 16627-79-5 (E) 3-methyl-1,3-butadienyl phenyl sulfide 
• 53588-13-9 Phenylsulfonyl-4-methyl-3-acetoxy-1-buten-2 
• 78-85-3 2-methylpropenal 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 

Downstream Products

• 410523-64-7 2-[5-((E)-2-benzenesulfonylvinyl)-5-methyl-4,5-dihydroisoxazol-3-yl]pyridine 
• 79998-91-7 3,7-dimethyl-5-oxo-2-octen-1-yl phenyl sulfone 
• 23985-25-3 2,6-dimethyl-octa-5,7-dien-4-one 
• 410523-63-6 5-((E)-2-benzenesulfonylvinyl)-5-methyl-3-phenyl-4,5-dihydroisoxazole 
• 79998-92-8 (E)-6-Benzenesulfonyl-2-(1-ethoxy-ethoxy)-2-isobutyl-4-methyl-hex-4-enenitrile 

Relevant articles and documents

Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Br?nsted acids. NMR and DFT study of these cations and their reactions

In strong Br?nsted acids (CF3SO3H, FSO3H, D2SO4), (arysulfonyl)allenes (ArSO2-CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO-CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO2-CR1=C-C(Me)=CH2, for R2 = R3 = Me, yields of 87-98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)-HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3, yields of 78-99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-diox-ides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.

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.

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(