67229-92-9

Basic information

• Product Name: Benzene, [(4-phenyl-1,3-butadienyl)sulfonyl]-, (E,E)-
• CAS NO: 67229-92-9
• Molecular Formula: C16H14O2S
• Molecular Weight: 270.352
• Mol File: 67229-92-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzene, [(4-phenyl-1,3-butadienyl)sulfonyl]-, (E,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(4-phenyl-1,3-butadienyl)sulfonyl]-, (E,E)-(67229-92-9)
• EPA Substance Registry System: Benzene, [(4-phenyl-1,3-butadienyl)sulfonyl]-, (E,E)-(67229-92-9)

Safety Data

• Hazardous Substances Data: 67229-92-9(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 873-55-2 sodium benzenesulfonate 
• 5535-48-8 PVS 
• 4363-35-3 Dihydroxy-styryl-boran 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 70960-88-2 trimethyl ((1E,3E)-4-phenylbuta-1,3-dien-1-yl)silane 
• 82480-46-4 C₂₂H₂₀O₄S₂ 

Downstream Products

• 1245924-56-4 1-(2-[(E,2R,3R)-5-phenyl-3-((phenylsulfonyl)methyl)pent-4-en-2-yl](S)-phenylsulfinyl)-4-methylbenzene 

Relevant articles and documents

PhI(OAc)2 mediated decarboxylative sulfonylation of β-aryl-α,β-unsaturated carboxylic acids: A synthesis of (E)-vinyl sulfones

A highly efficient metal-free decarboxylative sulfonylation protocol for the preparation of (E)-vinyl sulfones from of β-aryl-α,β-unsaturated carboxylic acids using sodium sulfinates and (diacetoxyiodo)benzene (PhI(OAc)2) was developed. This strategy offers a simple and expedient synthesis of (E)-vinyl sulfones bearing a wide variety of functional groups. A radical-based pathway has been proposed for this decarboxylative sulfonylation reaction.

Convenient synthesis of α,β-unsaturated sulfones via a Mizoroki-Heck reaction of arylboronic acids with phenyl vinyl sulfones

Palladium acetate catalyzed Mizoroki-Heck reaction of arylboronic acids with phenyl vinyl sulfones afford α,β-unsaturated sulfones in good yields.

First synthesis, X-ray structure analysis and reactions of alkenyltriphenylbismuthonium salts

Treatment of triphenylbismuth difluoride with alkenyltrimethylsilanes 1 or trimethylsilyl cyanidealkenyltrialkylstannanes 3 in the presence of boron trifluoride-diethyl ether gave the corresponding alkenyltriphenylbismuthonium tetrafluoroborates 2 in moderate to good yields. An X-ray crystallographic analysis of the salt 2e confirmed the distorted tetrahedral geometry of the central bismuth atom. When treated with a sulfinate 5 or the thiolate 11, the salts 2 readily transferred both the vinyl and phenyl moieties to these nucleophiles to afford the sulfones 7-10 or the sulfides 12, 13, respectively. In the presence of a palladium catalyst, the salt 2e underwent the Heck-type reaction with ethyl acrylate 17 to afford the dienoate 18 and cinnamate 19 in moderate yields. Action of KOBut on the salt 2b yielded p-tolylacetylene 22, while a similar reaction with the salt 2e in the presence of the styrenes 23 gave the cyclopropanes 24. A Hammett study of the latter reaction has suggested a possible involvement of an alkylidenecarbene as the intermediate in these base-promoted reactions.