86409-91-8

Upstream product

• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 764-93-2 1-decyne 
• 86409-85-0 (E)-2-(phenylseleno)-1-(p-tolylsulfonyl)-1-decene 
• 86409-98-5 C₂₃H₃₀O₃SSe 

Downstream Products

• 108895-58-5 2-[1-(Toluene-4-sulfonylmethyl)-nonylidene]-malonic acid dimethyl ester 

Relevant academic research and scientific papers

Substitution Reactions of Carbon Nucleophiles with β-(Phenylseleno)vinyl Sulfone Se Oxides

Selenoxides 2, obtained from the selenosulfonation and peracid oxidation of acetylenes, reacted with various nucleophiles to afford the products of overall substitution of the PhSeO moiety.Anions of dimethyl malonate, ethyl acetoacetate, malononitrile, 1-

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.