86409-90-7

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 1666-13-3 diphenyl diselenide 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 68819-94-3 p-tolyl benzeneselenosulfonate 

Downstream Products

• 87517-76-8 C₂₂H₂₀O₃SSe 
• 87517-84-8 C₁₆H₁₅⁽²⁾HO₃S 
• 87517-77-9 3-Phenyl-2-(p-tolylsulfonyl)-2-propen-1-ol 
• 108817-62-5 (Z)-2-phenyl-3-(p-tolylsulfonyl)-2-pentene 
• 108817-57-8 (Z)-2-phenyl-3-(p-tolylsulfonyl)-2-butene 

Relevant academic research and scientific papers

Synthesis of (E)-β-Selenovinyl Sulfones through a Multicomponent Regio- and Stereospecific Selenosulfonation of Alkynes with Insertion of Sulfur Dioxide

A novel and practical method for the selenosulfonation of alkynes with the insertion of sulfur dioxide has been developed. A series of β-(seleno)vinyl sulfones with high levels of regio- and stereoselectivity have been prepared. The key features of this reaction include a broad substrate scope, excellent functional-group tolerance, and amenability to scale-up synthesis. A plausible radical mechanism is proposed to illustrate this reaction.

Copper-Catalyzed Three Component Regio- and Stereospecific Selenosulfonation of Alkynes: Synthesis of (E)-β-Selenovinyl Sulfones

A copper-catalyzed highly regio- and stereospecific selenosulfonation of alkynes with arylsulfonohydrazides and diphenyl diselenide has been developed. This novel three component reaction proceeds under very mild conditions and with a broad scope of substrates, providing a wide range of (E)-β-selenovinyl sulfones in good to excellent yields.

Selenosulfonation of Acetylenes: Preparation of Novel β-(Phenylseleno)vinyl Sulfones and Their Conversion to Acetylenic and β-Functionalized Sulfones

The 1,2-additions of Se-phenyl p-tolueneselenosulfonate (1) to acetylenes under mild conditions afford β-(phenylseleno)vinyl sulfones 3, generally in high yields.The reaction is highly regioselective (anti-Markovnikov) and stereoselective (anti) and proceeds via a free-radical chain mechanism initiated by the thermolysis of the selenosulfonate.The oxidation of β-(phenylseleno)vinyl sulfones with m-chloroperbenzoic acid generates the corresponding selenoxides 4, which undergo syn or base-catalyzed elimination to furnish acetylenic sulfones 5.Base-catalyzed alcoholyses of selenoxides 4 in methanol or ethylene glycol produce β-keto sulfone ketals 8 or 10, respectively.Free β-keto sulfones 11 are formed by the acid-catalyzed hydrolysis of the corresponding β-(phenylseleno)vinyl sulfones 3.